Chicago, IL CHI to Boston, MA BOS flight with United

Sun, Nov 01
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The cheapest and fastest flights from Chicago, IL to Boston, MA

Showing times, prices and bookable tickets for Nov 01
Cheapest price on Nov 01
$224
Average ticket price on Nov 01
$464
Fastest journey on Nov 01
2 h 19 m
Average journey duration on Nov 01
2 h 23 m
Flights on Nov 01
67
Distance
1368 km
Cheap tickets

The best way to find a cheap flight ticket from Chicago, IL to Boston, MA is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from Chicago, IL to Boston, MA will cost around $464 if you buy it on the day, but the cheapest tickets can be found for only $224.

Fast flights

On Sun, Nov 01, we found 67 flights from Chicago, IL to Boston, MA, including 22 direct services.

On Sun, Nov 01 the direct flights cover the 1368 km distance in an average of 2 h 23 m but if you time it right, some flights will get you there in just 2 h 19 m .

On Sun, Nov 01 the longest flights will take 2 h 26 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

  • JetBlue AirwaysB61012
    0 transfers
  • JetBlue AirwaysB6112
    0 transfers
  • American AirlinesAA482
    0 transfers
  • American AirlinesAA3067
    0 transfers
  • American AirlinesAA1212
    0 transfers

Journey information

Overview: Chicago, IL to Boston, MA flight

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Icon of flight

Flights from Chicago, IL to Boston, MA depart on average 59 times per day, taking around 4h 7m. Cheap flight tickets for this journey start at $55 if you book in advance.

There are 17 flights per day. The earliest flight runs at 00:06, the last at 23:20. The fastest flight covers the 850 miles (1368 km) distance in 2h 14m. September is the cheapest month to fly.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance
850 miles (1368 km)
Average flight duration
4h 7m
Cheapest ticket price
$55
Flights per day
59
Direct flights
17
Fastest flight
2h 14m
First flight
12:06 AM
Last flight
11:20 PM
Cheapest Month
Sep
Cheapest Day
Tue
High Season
Jul - Sep
Low Season
Oct - Dec
Busiest Day
Sun
Least Busy Day
Fri
Best time to book
21 days
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information

Frequently asked questions about your Chicago, IL to Boston, MA trip

Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago, IL to Boston, MA.

Cheap plane tickets from Chicago, IL to Boston, MA can start from as little as $55 when you book in advance. The average flight ticket price for Chicago, IL to Boston, MA is $410 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The earliest flight from Chicago, IL to Boston, MA leaves at 12:06 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Boston, MA leaves at 11:20 PM.
Yes, there are 17 direct flights a day from Chicago, IL to Boston, MA with American Airlines, JetBlue Airways, United, Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.

Live departures

Chicago, IL to Boston, MA flight times

The table below shows live departures for Chicago, IL to Boston, MA flights for today, Saturday, October 31. You can also manually refresh the results below to see updated flight journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
UnitedUA2455 · UA3755:00 AM O'Hare International Airport
4h54
10:54 AM Edward L. Logan International Airport1 transfer
UnitedUA1982 · UA22115:30 AM O'Hare International Airport
7h57
2:27 PM Edward L. Logan International Airport1 transfer
American AirlinesAA1015+Republic AirlinesAA44685:59 AM O'Hare International Airport
5h15
12:14 PM Edward L. Logan International Airport1 transfer
American AirlinesAA29506:00 AM O'Hare International Airport
2h37
9:37 AM Edward L. Logan International Airport0 transfersDirect
UnitedUA656 · UA16696:00 AM O'Hare International Airport
5h26
12:26 PM Edward L. Logan International Airport1 transfer
UnitedUA5976 · UA6179 · UA13926:00 AM O'Hare International Airport
7h32
2:32 PM Edward L. Logan International Airport2 transfers
Republic AirlinesAA4543 · AA44086:43 AM O'Hare International Airport
4h16
11:59 AM Edward L. Logan International Airport1 transfer
UnitedUA2833 · UA12266:55 AM O'Hare International Airport
8h54
4:49 PM Edward L. Logan International Airport1 transfer
UnitedUA1217 · UA12326:59 AM O'Hare International Airport
7h31
3:30 PM Edward L. Logan International Airport1 transfer
UnitedUA1273 · UA16696:59 AM O'Hare International Airport
4h27
12:26 PM Edward L. Logan International Airport1 transfer
American AirlinesAA25117:00 AM O'Hare International Airport
2h33
10:33 AM Edward L. Logan International Airport0 transfersDirect
UnitedUA22137:00 AM O'Hare International Airport
2h19
10:19 AM Edward L. Logan International Airport0 transfersDirect
JetBlue AirwaysB6664 · B68707:00 AM O'Hare International Airport
11h12
7:12 PM Edward L. Logan International Airport1 transfer
UnitedUA2483 · UA12267:29 AM O'Hare International Airport
8h20
4:49 PM Edward L. Logan International Airport1 transfer
UnitedUA2092 · UA3688 · UA6888:00 AM O'Hare International Airport
9h57
6:57 PM Edward L. Logan International Airport2 transfers
envoy airAA4191+Republic AirlinesAA45178:02 AM O'Hare International Airport
3h56
12:58 PM Edward L. Logan International Airport1 transfer
American AirlinesAA1725 · AA31868:29 AM O'Hare International Airport
5h08
2:37 PM Edward L. Logan International Airport1 transfer
American AirlinesAA8028:30 AM O'Hare International Airport
2h37
12:07 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA318 · UA18468:40 AM O'Hare International Airport
9h59
7:39 PM Edward L. Logan International Airport1 transfer
UnitedUA1357 · UA13928:50 AM O'Hare International Airport
4h42
2:32 PM Edward L. Logan International Airport1 transfer
UnitedUA1357 · UA6888:50 AM O'Hare International Airport
9h07
6:57 PM Edward L. Logan International Airport1 transfer
American AirlinesAA2700+Republic AirlinesAA44948:52 AM O'Hare International Airport
5h14
3:06 PM Edward L. Logan International Airport1 transfer
UnitedUA11179:13 AM O'Hare International Airport
2h33
12:46 PM Edward L. Logan International Airport0 transfersDirect
American AirlinesAA315+Republic AirlinesAA44949:30 AM O'Hare International Airport
4h36
3:06 PM Edward L. Logan International Airport1 transfer
UnitedUA669 · UA3688 · UA68810:05 AM O'Hare International Airport
7h52
6:57 PM Edward L. Logan International Airport2 transfers
American AirlinesAA523+Republic AirlinesAA465710:08 AM O'Hare International Airport
5h39
4:47 PM Edward L. Logan International Airport1 transfer
UnitedUA1486 · UA68810:32 AM O'Hare International Airport
7h25
6:57 PM Edward L. Logan International Airport1 transfer
American AirlinesAA819+Republic AirlinesAA439710:34 AM O'Hare International Airport
5h24
4:58 PM Edward L. Logan International Airport1 transfer
UnitedUA160610:41 AM O'Hare International Airport
2h29
2:10 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA2857 · UA184610:55 AM O'Hare International Airport
7h44
7:39 PM Edward L. Logan International Airport1 transfer
American AirlinesAA253211:00 AM O'Hare International Airport
2h41
2:41 PM Edward L. Logan International Airport0 transfersDirect
American AirlinesAA903+Republic AirlinesAA443011:00 AM O'Hare International Airport
6h04
6:04 PM Edward L. Logan International Airport1 transfer
UnitedUA529 · UA3688 · UA68811:04 AM O'Hare International Airport
6h53
6:57 PM Edward L. Logan International Airport2 transfers
UnitedUA606 · UA354711:56 AM O'Hare International Airport
4h49
5:45 PM Edward L. Logan International Airport1 transfer
American AirlinesAA147912:06 PM O'Hare International Airport
2h43
3:49 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA1448 · UA52112:40 PM O'Hare International Airport
9h45
11:25 PM Edward L. Logan International Airport1 transfer
UnitedUA1448 · UA46212:40 PM O'Hare International Airport
7h48
9:28 PM Edward L. Logan International Airport1 transfer
American AirlinesAA3221+Republic AirlinesAA472412:52 PM O'Hare International Airport
5h37
7:29 PM Edward L. Logan International Airport1 transfer
UnitedUA2050 · UA13561:00 PM O'Hare International Airport
9h50
11:50 PM Edward L. Logan International Airport1 transfer
JetBlue AirwaysB61121:00 PM O'Hare International Airport
2h48
4:48 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA1695 · UA36951:07 PM O'Hare International Airport
4h32
6:39 PM Edward L. Logan International Airport1 transfer
American AirlinesAA830 · AA24041:22 PM O'Hare International Airport
4h52
7:14 PM Edward L. Logan International Airport1 transfer
UnitedUA1128 · UA6881:30 PM O'Hare International Airport
4h27
6:57 PM Edward L. Logan International Airport1 transfer
American AirlinesAA1632+Republic AirlinesAA47241:45 PM O'Hare International Airport
4h44
7:29 PM Edward L. Logan International Airport1 transfer
UnitedUA21011:59 PM O'Hare International Airport
2h25
5:24 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA1331 · UA6188 · UA7552:00 PM O'Hare International Airport
8h59
11:59 PM Edward L. Logan International Airport2 transfers
UnitedUA1658 · UA5212:22 PM O'Hare International Airport
8h03
11:25 PM Edward L. Logan International Airport1 transfer
UnitedUA587 · UA7552:29 PM O'Hare International Airport
8h30
11:59 PM Edward L. Logan International Airport1 transfer
UnitedUA767 · UA13562:30 PM O'Hare International Airport
8h20
11:50 PM Edward L. Logan International Airport1 transfer
American AirlinesAA24562:30 PM O'Hare International Airport
2h45
6:15 PM Edward L. Logan International Airport0 transfersDirect
American AirlinesAA2680+Republic AirlinesAA43822:52 PM O'Hare International Airport
5h54
9:46 PM Edward L. Logan International Airport1 transfer
UnitedUA6046 · UA6188 · UA7553:00 PM O'Hare International Airport
7h59
11:59 PM Edward L. Logan International Airport2 transfers
American AirlinesAA2840 · AA18743:37 PM O'Hare International Airport
5h12
9:49 PM Edward L. Logan International Airport1 transfer
UnitedUA2650 · UA26913:43 PM O'Hare International Airport
5h16
9:59 PM Edward L. Logan International Airport1 transfer
American AirlinesAA11623:48 PM O'Hare International Airport
2h45
7:33 PM Edward L. Logan International Airport0 transfersDirect
American AirlinesAA1315+Republic AirlinesAA46594:25 PM O'Hare International Airport
6h00
11:25 PM Edward L. Logan International Airport1 transfer
American AirlinesAA4075:11 PM O'Hare International Airport
2h48
8:59 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA23315:59 PM O'Hare International Airport
2h30
9:29 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA2202 · UA7556:12 PM O'Hare International Airport
4h47
11:59 PM Edward L. Logan International Airport1 transfer
American AirlinesAA31077:03 PM O'Hare International Airport
2h34
10:37 PM Edward L. Logan International Airport0 transfersDirect
American AirlinesAA26827:59 PM O'Hare International Airport
2h36
11:35 PM Edward L. Logan International Airport0 transfersDirect
JetBlue AirwaysB610128:24 PM O'Hare International Airport
2h44
12:08 AM Edward L. Logan International Airport0 transfersDirect
UnitedUA20718:30 PM O'Hare International Airport
2h28
11:58 PM Edward L. Logan International Airport0 transfersDirect
UnitedUA22969:20 PM O'Hare International Airport
2h26
12:46 AM Edward L. Logan International Airport0 transfersDirect

This is the last flight of the day.

Find all the dates and times for this journey

Why should you book Chicago, IL to Boston, MA flights with Omio?

American Airlines as well as JetBlue Airways, Spirit Airlines, United, Republic Airlines and more offer flights services from Chicago, IL to Boston, MA.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Boston, MA.

Why book with Omio vs American Airlines?

  • Compare with other providers: On Omio, you can not only buy tickets for American Airlines, but also compare tickets for the likes of JetBlue Airways, Spirit Airlines, United or Republic Airlines to find the best option for your trip from Chicago, IL to Boston, MA.
  • Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
  • Compare all your options: Omio allows you to compare American Airlines with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Chicago, IL to Boston, MA.

Why book with Omio over Trip, Edreams or Skyscanner?

  • Compare with other providers: On Omio, you can also compare tickets for the likes of JetBlue Airways, Spirit Airlines, United or Republic Airlines to find the best option for your trip from Chicago, IL to Boston, MA.
  • Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Chicago, IL to Boston, MA.

Airlines: United, American Airlines, Republic Airlines, JetBlue Airways, Spirit Airlines, Sun Country Airlines, skywest airlines from Chicago, IL to Boston, MAFind the best flights between Chicago, IL to Boston, MA with Omio's travel partners United, American Airlines, Republic Airlines, JetBlue Airways, Spirit Airlines, Sun Country Airlines, skywest airlines from $55. We can find you the best deals, schedules and tickets when comparing and booking the best trip.

United

About
United Airlines, established in 1926, is a major U.S. airline headquartered in Chicago, Illinois. Operating an extensive domestic and international network, United serves more destinations than any other airline, connecting travelers across six continents. The airline's eight hubs include Chicago–O'Hare, Denver, Houston–Intercontinental, Los Angeles, Newark, San Francisco, Washington–Dulles, and Guam. As a founding member of the Star Alliance, United offers a comprehensive range of services, including regional flights through United Express, catering to both leisure and business travelers. The airline is committed to sustainability, investing in sustainable aviation fuel and innovative technologies to reduce its environmental impact.
Luggage & cancellation policy
Average United Duration
2h 15m
Cheapest United Price
$88
United frequency
33 a day
Luggage included
Carry-on baggage allowance is 7kg total (2 pieces max. ) for both Choice and Flex fares on United Airlines and Virgin Australia flights.
Additional luggage
Excess baggage fees apply for additional checked luggage beyond the standard allowance.
Luggage storage
Both airlines provide checked baggage services for storing luggage during flights.
Cancellation Policy
Cancellation fees apply per person, per booking, with specific fees for different fare types.
Refund
Not applicable to flights; however, full refunds are available if flights are canceled by the airline.
Pregnant on board
Pregnant passengers are permitted to travel, with specific guidelines and medical certificates required after a certain gestational period.
Unaccompagned minor
Unaccompanied minors are permitted to travel, with specific age restrictions and services provided.
Amenities on board the airplane
Wifi
Food sold onboard
Meals and snacks are included on international flights operated by United Airlines and Virgin Australia.
Seat reservation
Seat selection may incur additional fees, depending on the fare type and airline.
Toilets
USB plugs
Accessibility
United Airlines and Virgin Australia offer services to and within Australia, providing accessible travel options for passengers with mobility needs.
Bikes
Both airlines permit bicycles onboard, with specific guidelines and fees.
Pets
United Airlines and Virgin Australia allow pets onboard, subject to specific policies and fees.
Learn more about United

JetBlue Airways

About
JetBlue Airways is a U.S.-based low-cost airline headquartered in Long Island City, New York. Established in 1998, it operates over 850 daily flights to 86 destinations across the U.S., Caribbean, and Latin America. The airline is known for its customer-friendly services, including complimentary Wi-Fi, free snacks, and spacious seating. JetBlue's fleet comprises various Airbus models, such as the A220, A320, and A321, as well as the Embraer E190. The company is committed to sustainability and has implemented initiatives to reduce its environmental impact. Joanna Geraghty serves as the CEO, leading a team of approximately 23,000 employees.
Luggage & cancellation policy
Average JetBlue Airways Duration
2h 14m
Cheapest JetBlue Airways Price
$66
JetBlue Airways frequency
4 a day
Luggage included
JetBlue's standard fare includes one checked bag and one carry-on bag.
Additional luggage
Additional luggage can be added for a fee, subject to availability.
Luggage storage
JetBlue offers overhead bin space for carry-on luggage and checked baggage services.
Cancellation Policy
JetBlue allows cancellations within 24 hours of booking for a full refund; after 24 hours, cancellation fees may apply.
Pregnant on board
JetBlue allows pregnant passengers to fly up to 36 weeks gestation without a medical certificate.
Unaccompagned minor
JetBlue allows unaccompanied minors aged 5-13 to travel for a fee, with specific guidelines.
Amenities on board the airplane
Wifi
Food sold onboard
JetBlue offers complimentary snacks and non-alcoholic beverages on all flights.
Seat reservation
JetBlue offers Even More Space seats for an additional fee, providing extra legroom and priority boarding.
Toilets
USB plugs
Accessibility
JetBlue Airways provides accessible services for passengers with disabilities, including wheelchair assistance and priority boarding.
Bikes
JetBlue accepts bicycles as checked baggage for a fee, with specific packaging requirements.
Pets
JetBlue allows pets in the cabin for a fee, with specific guidelines on pet carriers and weight limits.

American Airlines

About
American Airlines is one of the largest airlines in the world, connecting travelers to hundreds of destinations across the United States, Latin America, Europe, Asia, and beyond. Operating from major hubs such as Dallas/Fort Worth, Miami, and Charlotte, American offers a wide range of travel options. Passengers can choose from Economy with affordable fares, Premium Economy with extra space, or Business and First Class featuring flat-bed seats, premium dining, and lounge access. With a modern fleet and membership in the oneworld alliance, American Airlines combines global reach with comfort and reliability.
Luggage & cancellation policy
Average American Airlines Duration
2h 14m
Cheapest American Airlines Price
$55
American Airlines frequency
19 a day
Luggage included
1 carry-on bag (22 x 14 x 9 inches) and 1 personal item (18 x 14 x 8 inches) included in most fares
Additional luggage
Checked bags fees vary by route. First checked bag typically $30, second $40 on domestic flights
Cancellation Policy
Basic Economy tickets cannot be changed or refunded. Other fares allow changes with fee, refunds subject to fare rules.
Pregnant on board
Passengers can fly up to 36 weeks for single pregnancies, 32 weeks for multiple pregnancies. Medical certificate required within 7 days of departure if within 4 weeks of due date.
Unaccompagned minor
Children ages 5-14 can travel alone using American Airlines Unaccompanied Minor Service. Service fee is $150 each way.
Amenities on board the airplane
Wifi
Food sold onboard
USB plugs
Accessibility
American Airlines provides wheelchair assistance and special services for passengers with disabilities. Assistance must be requested at least 48 hours before departure.
Pets
Small dogs and cats allowed in cabin for $125 fee. Must be in approved carrier under seat. Service animals allowed.
Learn more about American Airlines

skywest airlines

About
SkyWest Airlines is a major North American regional airline headquartered in St. George, Utah. It operates flights for larger carriers such as Alaska Airlines (as Alaska SkyWest), American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express). SkyWest is the largest regional airline in North America by fleet size, passengers carried, and destinations served. The airline connects passengers to over 250 destinations across the United States, Canada, and Mexico, primarily linking smaller airports to major airline hubs. SkyWest's fleet consists of regional jets, including the Bombardier CRJ series and Embraer 175 aircraft.
Luggage & cancellation policy
Average skywest airlines Duration
3h 28m
Cheapest skywest airlines Price
$729
skywest airlines frequency
1 a day
Luggage included
One carry-on bag and one personal item are allowed for free.
Additional luggage
Additional luggage can be purchased, and fees apply for excess, oversized, or overweight baggage.
Cancellation Policy
If canceled within 24 hours of purchase, a full refund is possible, provided the departure is at least 7 days away; after 24 hours, fees range from $100 to $500.
Refund
If SkyWest Airlines cancels a flight, passengers are eligible for a full refund.
Pregnant on board
Being pregnant on board is allowed, but specific policies may depend on the partner airline.
Unaccompagned minor
Children aged 5-14 can travel alone using the unaccompanied minor service, which includes airport escort and supervision.
Amenities on board the airplane
Seat reservation
Toilets
Accessibility
SkyWest Airlines complies with all provisions of the Air Carrier Access Act and accommodates customers with special needs.
Bikes
Bicycles can be checked in but may incur additional fees and must be properly packed.
Pets
Small pets like cats and dogs are allowed in the cabin for a fee, with restrictions on pet and carrier size.

Sun Country Airlines

Luggage & cancellation policy
Average Sun Country Airlines Duration
4h 26m
Cheapest Sun Country Airlines Price
$158
Sun Country Airlines frequency
1 a day
Luggage included
One personal item (17 x 13 x 9 inches) included
Additional luggage
Checked bags available for purchase, fees vary by route
Cancellation Policy
Refunds available within 24 hours of booking, after that fees apply based on fare type
Pregnant on board
Pregnant passengers can travel up to 36 weeks (32 weeks for multiple pregnancies). Medical certificate required after 28 weeks
Unaccompagned minor
Unaccompanied minor service available for children 5-14 years old, fee applies, must be booked in advance
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Wheelchair assistance available with 48-hour advance notice

Republic Airlines

About
Republic Airways is a major regional airline in the United States, operating as a subsidiary of Republic Airways Holdings. It provides scheduled passenger service for American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express) using a fleet of Embraer 170 and 175 regional jets. Headquartered in Indianapolis, Indiana, Republic Airways operates over 900 daily flights to more than 80 cities across the U.S. and Canada. The company is known for its large fleet of Embraer E-Jets and its state-of-the-art training facilities. In April 2025, Republic Airways Holdings announced its acquisition of Mesa Air Group, which is expected to create the second-largest regional carrier in the U.S.
Luggage & cancellation policy
Average Republic Airlines Duration
2h 26m
Cheapest Republic Airlines Price
$61
Republic Airlines frequency
4 a day
Luggage included
One carry-on bag (24 x 16 x 10) and one personal item
Additional luggage
Checked bags for a fee
Cancellation Policy
Tickets are non-refundable but may be cancelled for future flight credit minus applicable fees
Pregnant on board
Passengers can fly up to the end of their 36th week for single pregnancies and the end of their 32nd week for multiple pregnancies
Unaccompagned minor
Unaccompanied minor service is available for children ages 5-14. Must be booked directly with Republic Airlines
Amenities on board the airplane
USB plugs
Accessibility
Republic Airlines offers assistance for passengers with reduced mobility, including wheelchair services and priority boarding. Passengers are advised to request these services in advance to ensure availability and proper arrangements.

Spirit Airlines

About
Spirit Airlines is an American ultra-low-cost carrier, headquartered in Dania Beach, Florida, operating scheduled flights throughout the United States, the Caribbean, and Latin America. Known for its distinctive bright yellow planes, Spirit's business model traditionally focuses on offering low base fares by unbundling services, allowing passengers to pay only for the amenities they choose, such as baggage and seat selection. As of August 2024, Spirit is evolving its offerings, introducing new fare tiers like "Go Big," "Go Comfy," "Go Savvy," and "Go," which include various bundled perks such as wider seats, extra legroom, priority boarding, and in-flight refreshments. Spirit was the seventh largest passenger carrier in North America as of 2023.
Luggage & cancellation policy
Average Spirit Airlines Duration
4h 19m
Cheapest Spirit Airlines Price
$73
Spirit Airlines frequency
2 a day
Luggage included
Personal item (18 x 14 x 8 inches) included
Additional luggage
Checked bags: First bag $79-89, Second bag $89-99, Additional bags $105-110
Cancellation Policy
Cancellation within 24 hours of booking is free, after that fees apply based on fare type and timing
Pregnant on board
Up to 7 days before departure with medical certificate. After 28 weeks, medical certificate required
Unaccompagned minor
Ages 5-14 can travel as unaccompanied minors for $100 fee per direction. Service not available on international flights or connecting flights
Amenities on board the airplane
Wifi
Accessibility
Spirit Airlines offers assistance for passengers with disabilities, including wheelchair services and priority boarding. Passengers are encouraged to request assistance at least 48 hours in advance to ensure availability.
Learn more about Spirit Airlines

Companies, tickets, and onboard amenities between Chicago, IL and Boston, MA

Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.

When taking a flight from Chicago, IL to Boston, MA, you can count on American Airlines, JetBlue Airways, Spirit Airlines, United, Republic Airlines, Sun Country Airlines, skywest airlines for the best way to get you to Boston, MA. You can also check all possible airlines who offer a service between Chicago, IL and Boston, MA and compare the amenities they offer before buying a plane ticket.
For international flights we recommend to arrive 2.5 to 3 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.

Complete guide to Boston, MA

Things to do in Boston, MA

Discover the best of Boston, MA — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Boston, MA trip today.

  • Must visit

Museum of Fine Arts, Boston

Major art museum with encyclopedic collections, from ancient works to Impressionism, in a grand and highly walkable campus.

View on mapVisit website
  • Must visit

Isabella Stewart Gardner Museum

Unique museum displaying Isabella Stewart Gardner's art collection in a Venetian-style palace with a beautiful courtyard.

View on mapVisit website
  • Must visit

Museum of Science

Hands-on science museum on the Charles River, popular for interactive exhibits, live presentations, and family-friendly learning.

View on mapVisit website

US dollar ($)

Boston is pricier than many US cities. Hotels, dining, and attractions add up fast, though transit is manageable and budget food options exist.

Average meal costs

Budget
$10-18 for fast food or casual takeout.
Mid-range
$25-45 per person for a mid-range restaurant meal.
Fine dining
$75+ per person for upscale dining.
Coffee
$3-6 for drip coffee or cappuccino.

Tipping culture

Tip 18-20% at restaurants, more for excellent service. Taxis: 10-15%. Cafes: round up or add $1 per drink.

Plan your visit to Boston, MA

Get destination-focused answers for the end of your trip, including what to do, when to go, practical entry details, and tips for making the most of your time in Boston, MA.

The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Boston, MA, travelers should be aware of pickpocketing and bag theft, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and overcharging by unlicensed taxi drivers. It's advisable to use official transportation services, stay alert in busy areas, and avoid sharing personal information with strangers to ensure safety.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.

FAQs: Chicago, IL to Boston, MA Flight

Find answers to the most common questions about traveling from Chicago, IL to Boston, MA by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Boston, MA, this guide helps you travel smarter and with confidence.

FAQs
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Boston, MA including taking a train, bus, and flight.

popular airports

Popular airports from Chicago, IL to Boston, MA

Most Chicago, IL to Boston, MA flights use the O'Hare International Airport to Edward L. Logan International Airport airport pair. Use this guide to compare Chicago, IL and Boston, MA airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.

Departure airports in Chicago
Arrival airports in Boston

Which Chicago, IL airport do flights to Boston, MA leave from?

Flights from Chicago, IL to Boston, MA depart from O'Hare International Airport. The airport is 2 miles (4 km) from Chicago, IL city centre at 10000 W O'Hare Ave, Chicago, IL 60666, USA.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USAWifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rental
City-centre transport

Getting to O'Hare International Airport from Chicago city centre

O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:

SubwayBlue Line · 1h 7m · $6 · every ~23 min

O'Hare International Airport airport facilities and services

O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.

Food and drink

Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.

Wi-Fi and ATMs

Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.

Luggage and lost property

Lost and found is available at the station.

Parking, taxis and toilets

Available at O'Hare International Airport: Parking, Taxis, WC.

Bike and car services

Available at O'Hare International Airport: Car Rental.

Accessibility

Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.

Shops, hotels and contact

Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..

More about O'Hare International Airport

Airports for flights from Chicago, IL to Boston, MA

See which airports are used for flights between Chicago, IL and Boston, MA, including airport details.

Flights from Chicago, IL to Boston, MA generally leave from O'Hare International Airport and arrive in Edward L. Logan International Airport.O'Hare International Airport is 2 miles (4 km) away from Chicago, IL city centre and Edward L. Logan International Airport is 1 miles (3 km) from Boston, MA city centre.

More options for your journey from Chicago, IL to Boston, MA

Here are some other resources that might have the information you need

Return journeys for flights from Boston, MA to Chicago, IL
Buses from Chicago, IL to Boston, MA
Trains from Chicago, IL to Boston, MA
More information on flights to Chicago, IL
More information on flights to Boston, MA

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