Journey information
Overview: Chicago, IL to Boston, MA flight
Flights from Chicago, IL to Boston, MA depart on average 42 times per day, taking around 2h 35m. Cheap flight tickets for this journey start at $50 (€40) if you book in advance.
There are 10 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. April is the cheapest month to fly.
Distance 850 miles (1368 km) |
Average flight duration 2h 35m |
Cheapest ticket price $50 (€40) |
Flights per day 42 |
Direct flights 10 |
Fastest flight 2h 14m |
First flight 12:06 AM |
Last flight 11:20 PM |
Cheapest Month Apr |
Cheapest Day Tue |
High Season Jul - Sep |
Low Season Apr - Jun |
Busiest Day Sun |
Least Busy Day Thu |
Best time to book 70 days |
The cheapest and fastest flights from Chicago, IL to Boston, MA
Cheapest price
$50
Average price
$113
Fastest journey
2 h 16 m
Average duration
2 h 21 m
Flights per day
5
Distance
1368 km
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 $113 if you buy it on the day, but the cheapest tickets can be found for only $50.
Of the 5 flights that leave Chicago, IL for Boston, MA onMon, May 04, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, May 04 the direct flights cover the 1368 km distance in an average of 2 h 21 m but if you time it right, some flights will get you there in just 2 h 16 m .
On Mon, May 04 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.
2:05 PM2h20Chicago, IL4:25 PMBoston, MA$501One-way0 transfers
2:00 AM2h16Chicago, IL4:16 AMBoston, MA$741One-way0 transfers
10:27 PM2h28Chicago, IL12:55 AMBoston, MA$1121One-way0 transfers
7:15 PM2h17Chicago, IL9:32 PMBoston, MA$1201One-way0 transfers
2:25 AM2h32Chicago, IL4:57 AMBoston, MA$2071One-way0 transfers
2:00 AM2h16Chicago, IL4:16 AMBoston, MA$741One-way0 transfers
7:15 PM2h17Chicago, IL9:32 PMBoston, MA$1201One-way0 transfers
2:05 PM2h20Chicago, IL4:25 PMBoston, MA$501One-way0 transfers
1:40 PM2h25Chicago, IL4:05 PMBoston, MA$2471One-way0 transfers
2:55 PM2h26Chicago, IL5:21 PMBoston, MA$2441One-way0 transfers
Travel Information
Compare train, bus, and flight for Chicago, IL to Boston, MA
Omio recommends booking the flight as it is the most popular option from Chicago, IL to Boston, MA among Omio's users. If you are prioritising price take the flight with prices starting from $50. For those with little time consider booking a flight which can get you there in 2h 35m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.4 - 1.2kg. The ticket price range depends on the travel mode: a flight costs an average of $50, and a train costs an average of $92.
Distance: 850 miles (1368 km)
Compare flight with
Most popular Flight | Train | Bus |
|---|---|---|
$172 Average price Cheapest | $321 Average price | $206 Average price |
5h 35m Average total duration Fastest 2h 35m Onboard + 3h 0m Additional time* | 22h 32m Average total duration 22h 2m Onboard + 30m Additional time* | 25h 40m Average total duration 25h 10m Onboard + 30m Additional time* |
4.1 - 8.2kg CO2 emissions | 0.4 - 1.2kg CO2 emissions Lowest | 1.4 - 3.4kg CO2 emissions |
![]() Most popular airline | ![]() Most popular train company | ![]() Most popular bus company |
Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
Live departures
Chicago, IL to Boston, MA flight times
The table below shows live departures for Chicago, IL to Boston, MA flights for today, Sunday, May 3. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 12:51 PM Chicago, IL | 2h27 | 3:18 PM Boston, MA | 0 transfersDirect | |
![]() | 4:12 PM Chicago, IL | 12h41 | 4:53 AM Boston, MA | 0 transfersDirect | |
![]() | 7:15 PM Chicago, IL | 2h17 | 9:32 PM Boston, MA | 0 transfersDirect | |
| Monday, May 4 | |||||
![]() | 1:41 AM Chicago, IL | 2h29 | 4:10 AM Boston, MA | 0 transfersDirect | |
![]() | 2:00 AM Chicago, IL | 2h16 | 4:16 AM Boston, MA | 0 transfersDirect | |
![]() | 2:25 AM Chicago, IL | 2h32 | 4:57 AM Boston, MA | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
How far in advance should I book flight tickets from Chicago, IL to Boston, MA?
Compare prices and tickets Chicago, IL to Boston, MA by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Why should you book Chicago, IL to Boston, MA flights with Omio?
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: American Airlines, JetBlue Airways, Spirit Airlines, United, Republic Airlines from Chicago, IL to Boston, MAFind the best flights between Chicago, IL to Boston, MA with Omio's travel partners American Airlines, JetBlue Airways, Spirit Airlines, United, Republic Airlines from $50 (€40). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
JetBlue Airways
United
American Airlines
Spirit Airlines
Republic Airlines
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.

- Boston Marathon, the world's oldest annual marathon attracting elite runners and thousands of spectators
- Boston Calling Music Festival, a three-day music festival featuring top artists across various genres
- Independence Day Celebration on the Esplanade, a spectacular fireworks display and concert celebrating America's birthday along the Charles River.
- Best sights: Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 significant historical sites
- Fenway Park, the iconic baseball stadium and home of the Boston Red Sox
- Museum of Fine Arts, one of the largest art museums in the United States with an extensive collection of artworks
- Boston Common, the oldest public park in the United States offering green space and historical landmarks
- New England Aquarium, a popular attraction featuring a wide variety of marine life and interactive exhibits.
- Patriot's Day, commemorates the start of the American Revolution with reenactments and parades
- Memorial Day, marks the unofficial start of summer with vibrant outdoor activities and events
- Labor Day, offers pleasant weather and a chance to enjoy the city's parks and waterfront.
- Things to do: Explore the historic streets of Beacon Hill, known for its charming cobblestone streets and Federal-style rowhouses
- Take a scenic walk along the Charles River Esplanade, offering beautiful views of the Boston skyline
- Visit the Boston Public Library, a stunning architectural landmark with impressive collections and exhibits
- Enjoy a guided tour of the historic USS Constitution, the world's oldest commissioned naval vessel still afloat
- Discover the vibrant atmosphere of Quincy Market, with its diverse food stalls and unique shops.
popular airports
Popular airports from Chicago, IL to Boston, MA
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
- Available outside the terminal.
- Elevators, ramps, toilets
- Available throughout the airport.
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
- Lounges available, including United Club and American Airlines Admirals Club.
- Lost and Found located in terminal 1, near the baggage claim area.
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
- CTA Blue Line, O'Hare Station, 45 minutes to city center
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including Duty-Free and Hudson News.
- Parking available in Central Parking Garage, Economy Parking, and terminal B Garage, approximately 7.6€ ($8) per hour.
- Restaurants are available in all terminals, including Legal Sea Foods (seafood) and Wahlburgers (American).
- Available outside the terminal.
- Elevators, ramps
- Available throughout the airport.
- Hotels within walking distance, including Hilton Boston Logan Airport.
- Showers are available in some lounges; access may require a lounge pass or membership.
- Lounges available, including The Club and Delta Sky Club.
- Lost and Found located in the Lost & Found Office in terminal C.
- Car rental services are available at the Rental Car Center, accessible by shuttle.
- MBTA Blue Line, Airport Station, 5 km
More options for your journey from Chicago, IL to Boston, MA
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