- Must visit
Portland Museum of Art
Leading regional museum with strong American and European art, notable Winslow Homer works, and a handsome historic campus.
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The cheapest and fastest flights from Chicago, IL to Portland, ME
Showing times, prices and bookable tickets for Oct 31
- Cheapest price on Oct 31
- $224
- Average ticket price on Oct 31
- $478
- Fastest journey on Oct 31
- 2 h 26 m
- Average journey duration on Oct 31
- 2 h 56 m
- Flights on Oct 31
- 56
- Distance
- 1432 km
Cheap tickets
The best way to find a cheap flight ticket from Chicago, IL to Portland, ME 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 Portland, ME will cost around $478 if you buy it on the day, but the cheapest tickets can be found for only $224.
Fast flights
On Sat, Oct 31, we found 56 flights from Chicago, IL to Portland, ME, including 4 direct services.
On Sat, Oct 31 the direct flights cover the 1432 km distance in an average of 2 h 56 m but if you time it right, some flights will get you there in just 2 h 26 m .
On Sat, Oct 31 the longest flights will take 4 h 25 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.
AA47418:45 AM 2h46 O'Hare International Airport 12:31 PM Portland International Jetport $224 1 One-way 0 transfers- AA4478
1:44 PM 2h31 O'Hare International Airport 5:15 PM Portland International Jetport $224 1 One-way 0 transfers 
AA903 · AA209811:00 AM 4h47 O'Hare International Airport 4:47 PM Portland International Jetport $234 1 One-way 1 transfer- AA2345 · AA2355
7:55 AM 6h48 O'Hare International Airport 3:43 PM Portland International Jetport $234 1 One-way 1 transfer - AA3161 · AA2098
8:10 AM 7h37 O'Hare International Airport 4:47 PM Portland International Jetport $234 1 One-way 1 transfer
UA42210:50 AM 2h26 O'Hare International Airport 2:16 PM Portland International Jetport $278 1 One-way 0 transfers- AA4478
1:44 PM 2h31 O'Hare International Airport 5:15 PM Portland International Jetport $224 1 One-way 0 transfers - UA1401
6:15 PM 2h33 O'Hare International Airport 9:48 PM Portland International Jetport $278 1 One-way 0 transfers - AA4741
8:45 AM 2h46 O'Hare International Airport 12:31 PM Portland International Jetport $224 1 One-way 0 transfers - AA327+AA4571
6:00 AM 4h25 O'Hare International Airport 11:25 AM Portland International Jetport $234 1 One-way 1 transfer
Journey information
Overview: Chicago, IL to Portland, ME flight
USAUSA
Flights from Chicago, IL to Portland, ME depart on average 49 times per day, taking around 4h 11m. Cheap flight tickets for this journey start at $155 (€131) but you can travel from only $78 (€65) by bus.
There are 4 flights per day. The earliest flight runs at 05:00, the last at 21:40. The fastest flight covers the 889 miles (1432 km) distance in 2h 19m. October 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
Cheapest alternative travel mode
Bus from $78 (€65)
Distance 889 miles (1432 km) |
Average flight duration 4h 11m |
Cheapest ticket price $155 (€131) |
Flights per day 49 |
Direct flights 4 |
Fastest flight 2h 19m |
First flight 5:00 AM |
Last flight 9:40 PM |
Cheapest Month Oct |
Cheapest Day Wed |
High Season Jul - Sep |
Low Season Jan - Mar |
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
Cheapest alternative travel mode
Bus from $78 (€65)
Frequently asked questions about your Chicago, IL to Portland, ME trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago, IL to Portland, ME.
Cheap plane tickets from Chicago, IL to Portland, ME can start from as little as $155 (€131) when you book in advance. The average flight ticket price for Chicago, IL to Portland, ME is $534 (€449) ; 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 Portland, ME leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Chicago, IL to Portland, ME leaves at 9:40 PM.
Yes, there are 4 direct flights a day from Chicago, IL to Portland, ME with Republic Airlines, United, skywest airlines. Schedules can vary on holidays or weekends with fewer direct flights.
Live departures
Chicago, IL to Portland, ME flight times
The table below shows live departures for Chicago, IL to Portland, ME flights for today, Friday, October 30. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| AA2842 · AA1747 | 5:00 AM O'Hare International Airport | 5h26 | 11:26 AM Portland International Jetport | 1 transfer | |
| UA1055 · UA3709 | 5:55 AM O'Hare International Airport | 7h32 | 2:27 PM Portland International Jetport | 1 transfer | |
| UA5976 · UA6179 · UA3709 | 6:00 AM O'Hare International Airport | 7h27 | 2:27 PM Portland International Jetport | 2 transfers | |
| AA1784 · AA1744 | 6:29 AM O'Hare International Airport | 8h09 | 3:38 PM Portland International Jetport | 1 transfer | |
| UA3566 · UA3436 · UA3709 | 6:50 AM O'Hare International Airport | 6h37 | 2:27 PM Portland International Jetport | 2 transfers | |
| AA2997 · AA2355 | 6:59 AM O'Hare International Airport | 7h44 | 3:43 PM Portland International Jetport | 1 transfer | |
| UA1273 · UA4478 | 6:59 AM O'Hare International Airport | 5h27 | 1:26 PM Portland International Jetport | 1 transfer | |
| UA1217 · UA397 | 7:00 AM O'Hare International Airport | 8h02 | 4:02 PM Portland International Jetport | 1 transfer | |
| UA1488 · UA1992 · UA4498 | 7:15 AM O'Hare International Airport | 10h37 | 6:52 PM Portland International Jetport | 2 transfers | |
| AA2345 · AA2355 | 7:48 AM O'Hare International Airport | 6h55 | 3:43 PM Portland International Jetport | 1 transfer | |
| AA411 · AA1744 | 8:05 AM O'Hare International Airport | 6h33 | 3:38 PM Portland International Jetport | 1 transfer | |
AA1725+ AA5127 | 8:29 AM O'Hare International Airport | 6h40 | 4:09 PM Portland International Jetport | 1 transfer | |
| AA4741 | 8:45 AM O'Hare International Airport | 2h46 | 12:31 PM Portland International Jetport | 0 transfersDirect | |
| UA1357 · UA3709 | 8:50 AM O'Hare International Airport | 4h37 | 2:27 PM Portland International Jetport | 1 transfer | |
| AA2700 · AA2355 | 8:52 AM O'Hare International Airport | 5h51 | 3:43 PM Portland International Jetport | 1 transfer | |
| UA3422 · UA1892 · UA4498 | 9:00 AM O'Hare International Airport | 8h52 | 6:52 PM Portland International Jetport | 2 transfers | |
| AA2080 · AA1744 | 9:02 AM O'Hare International Airport | 5h36 | 3:38 PM Portland International Jetport | 1 transfer | |
| AA315 · AA2355 | 9:30 AM O'Hare International Airport | 5h13 | 3:43 PM Portland International Jetport | 1 transfer | |
| UA669 · UA3688 · UA3664 | 10:05 AM O'Hare International Airport | 7h57 | 7:02 PM Portland International Jetport | 2 transfers | |
| AA523 · AA2355 | 10:08 AM O'Hare International Airport | 4h35 | 3:43 PM Portland International Jetport | 1 transfer | |
| AA3128 · AA2098 | 10:10 AM O'Hare International Airport | 5h47 | 4:57 PM Portland International Jetport | 1 transfer | |
| UA1486 · UA3664 | 10:32 AM O'Hare International Airport | 7h30 | 7:02 PM Portland International Jetport | 1 transfer | |
| UA2389 · UA1892 · UA4498 | 10:45 AM O'Hare International Airport | 7h07 | 6:52 PM Portland International Jetport | 2 transfers | |
| UA5756 · UA6190 · UA3664 | 10:47 AM O'Hare International Airport | 7h15 | 7:02 PM Portland International Jetport | 2 transfers | |
| UA422 | 10:50 AM O'Hare International Airport | 2h26 | 2:16 PM Portland International Jetport | 0 transfersDirect | |
| UA529 · UA3688 · UA3664 | 11:00 AM O'Hare International Airport | 7h02 | 7:02 PM Portland International Jetport | 2 transfers | |
| AA903 · AA2098 | 11:10 AM O'Hare International Airport | 4h47 | 4:57 PM Portland International Jetport | 1 transfer | |
| AA662 · AA497 | 12:05 PM O'Hare International Airport | 5h39 | 6:44 PM Portland International Jetport | 1 transfer | |
| UA3645 · UA687 · UA1397 | 12:59 PM O'Hare International Airport | 9h22 | 11:21 PM Portland International Jetport | 2 transfers | |
| AA1409 · AA2120 | 1:17 PM O'Hare International Airport | 8h19 | 10:36 PM Portland International Jetport | 1 transfer | |
| AA830+AA5129 | 1:22 PM O'Hare International Airport | 4h34 | 6:56 PM Portland International Jetport | 1 transfer | |
| AA4478 | 1:29 PM O'Hare International Airport | 2h35 | 5:04 PM Portland International Jetport | 0 transfersDirect | |
| UA1128 · UA3664 | 1:30 PM O'Hare International Airport | 4h32 | 7:02 PM Portland International Jetport | 1 transfer | |
| UA1331 · UA6188 · UA4577 | 2:00 PM O'Hare International Airport | 8h59 | 11:59 PM Portland International Jetport | 2 transfers | |
| UA1502 · UA687 · UA1397 | 2:21 PM O'Hare International Airport | 8h00 | 11:21 PM Portland International Jetport | 2 transfers | |
| UA4644 · UA6362 · UA4577 | 2:30 PM O'Hare International Airport | 8h29 | 11:59 PM Portland International Jetport | 2 transfers | |
| UA1236 · UA1397 | 2:38 PM O'Hare International Airport | 7h43 | 11:21 PM Portland International Jetport | 1 transfer | |
| UA398 · UA6188 · UA4577 | 3:00 PM O'Hare International Airport | 7h59 | 11:59 PM Portland International Jetport | 2 transfers | |
| AA2840+AA5285 | 3:37 PM O'Hare International Airport | 5h54 | 10:31 PM Portland International Jetport | 1 transfer | |
| AA2840 · AA652 | 3:37 PM O'Hare International Airport | 6h59 | 11:36 PM Portland International Jetport | 1 transfer | |
| UA2650 · UA1397 | 3:40 PM O'Hare International Airport | 6h41 | 11:21 PM Portland International Jetport | 1 transfer | |
| UA1630 · UA1397 | 4:40 PM O'Hare International Airport | 5h41 | 11:21 PM Portland International Jetport | 1 transfer | |
| AA1848+AA5285 | 4:50 PM O'Hare International Airport | 4h41 | 10:31 PM Portland International Jetport | 1 transfer | |
| AA2769 · AA2978 | 4:50 PM O'Hare International Airport | 6h09 | 11:59 PM Portland International Jetport | 1 transfer | |
| AA1848 · AA652 | 4:50 PM O'Hare International Airport | 5h46 | 11:36 PM Portland International Jetport | 1 transfer | |
| AA1743 · AA652 | 5:29 PM O'Hare International Airport | 5h07 | 11:36 PM Portland International Jetport | 1 transfer | |
| UA378 · UA1397 | 5:30 PM O'Hare International Airport | 4h51 | 11:21 PM Portland International Jetport | 1 transfer | |
| UA2458 · UA397 | 5:48 PM O'Hare International Airport | 21h14 | 4:02 PM Portland International Jetport | 1 transfer | |
| AA489 · AA2978 | 5:50 PM O'Hare International Airport | 5h09 | 11:59 PM Portland International Jetport | 1 transfer | |
| UA2202 · UA4577 | 6:07 PM O'Hare International Airport | 4h52 | 11:59 PM Portland International Jetport | 1 transfer | |
| UA1401 | 6:18 PM O'Hare International Airport | 2h34 | 9:52 PM Portland International Jetport | 0 transfersDirect | |
| UA329 · UA397 | 7:57 PM O'Hare International Airport | 19h05 | 4:02 PM Portland International Jetport | 1 transfer | |
| AA4504 | 8:00 PM O'Hare International Airport | 2h40 | 11:40 PM Portland International Jetport | 0 transfersDirect | |
| UA2148 · UA397 | 9:00 PM O'Hare International Airport | 18h02 | 4:02 PM Portland International Jetport | 1 transfer | |
| UA590 · UA397 | 9:47 PM O'Hare International Airport | 17h15 | 4:02 PM Portland International Jetport | 1 transfer | |
Find all the dates and times for this journey
Why should you book Chicago, IL to Portland, ME flights with Omio?
Republic Airlines as well as United, American Airlines, JetBlue Airways, skywest airlines and more offer flights services from Chicago, IL to Portland, ME.
Omio is the only official third party seller for Republic Airlines tickets.
Why book with Omio vs Republic Airlines?
- Compare with other providers: On Omio, you can not only buy tickets for Republic Airlines, but also compare tickets for the likes of United, American Airlines, JetBlue Airways or skywest airlines to find the best option for your trip from Chicago, IL to Portland, ME.
- 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 Republic 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 Portland, ME.
Airlines: United, American Airlines, Republic Airlines, JetBlue Airways, skywest airlines from Chicago, IL to Portland, MEFind the best flights between Chicago, IL to Portland, ME with Omio's travel partners United, American Airlines, Republic Airlines, JetBlue Airways, skywest airlines from $78 (€65). 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 19m
Cheapest United Price
$199 (€167)
United frequency
27 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.
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
3h 42m
Cheapest JetBlue Airways Price
$225 (€189)
JetBlue Airways frequency
3 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 36m
Cheapest American Airlines Price
$155 (€131)
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.
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
2h 25m
Cheapest skywest airlines Price
$407 (€343)
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.
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 35m
Cheapest Republic Airlines Price
$213 (€179)
Republic Airlines frequency
3 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.
Companies, tickets, and onboard amenities between Chicago, IL and Portland, ME
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 Portland, ME, you can count on Republic Airlines, United, American Airlines, JetBlue Airways, skywest airlines for the best way to get you to Portland, ME. You can also check all possible airlines who offer a service between Chicago, IL and Portland, ME 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 Portland, ME
Things to do in Portland, ME
Discover the best of Portland, ME — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Portland, ME trip today.
- Recommended
Portland Head Light Museum
Hands-on history museum inside Portland Head Light exploring lighthouse technology, shipwrecks, and Maine's maritime past.
- Recommended
Wadsworth-Longfellow House Museum
Historic home and museum focused on Henry Wadsworth Longfellow, with original furnishings and insight into early Portland life.
- Must visit
Old Port
Historic district of brick streets, shops, and harbor views; Portland's classic place to stroll, browse, and absorb local character.
- Must visit
Eastern Promenade
Eastern Promenade offers broad Casco Bay views, walking paths, lawns, and one of Portland's best spots for relaxing outdoors.
- Recommended
Munjoy Hill
Hilltop neighborhood with historic homes, local feel, and rewarding lookout points around the Portland Observatory area.
- Gluten-free
Maine Lobster
Sweet, cold-water Maine lobster served steamed, in rolls, or with drawn butter. It is the city’s signature catch and a cornerstone of working waterfront food culture.
Clam Chowder
A creamy New England-style chowder made with local clams, potatoes, and salt pork. It is a classic Maine coastal comfort dish found across Portland.
- Gluten-free
Maine Oysters
Freshly shucked oysters from Maine farms such as the Damariscotta River. They are prized for their cold-water brininess and strong connection to local aquaculture.
Fore Street
Refined destination restaurant serving seasonal Maine tasting menus with local seafood and produce. Elegant but warm, and one of Portland’s top fine dining rooms.
The Holy Donut
Historic market-style venue known for potato donuts, sandwiches, coffee, and local pantry goods. Casual, busy, and deeply rooted in Portland food culture.
Eventide Oyster Co.
Beloved casual seafood shack known for excellent lobster rolls, fried seafood, and harbor views. A classic Portland stop with a relaxed waterfront feel.
United States Dollar ($)
Moderate for a U.S. coastal city: hotels peak in summer, seafood dining is mid-priced to high, and local transit is limited so visitors may rely on walking, rideshares, or cars.
Average meal costs
- Budget
- $10-18 for fast food, deli, or casual takeaway.
- Mid-range
- $20-40 per person for a casual sit-down meal.
- Fine dining
- $60+ per person at upscale restaurants.
- Coffee
- $3-6 for drip coffee or a cappuccino.
Tipping culture
Tip 18-20% at restaurants, 15-20% for taxis, and $1-2 per drink or coffee at cafes and bars.
Plan your visit to Portland, ME
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 Portland, ME.
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 Portland, ME, travelers should be cautious of petty theft, especially in crowded areas like the Old Port district. Common scams include overcharging by unlicensed taxi or ride-share drivers and parking meter fraud. It’s advisable to use official transportation services and remain vigilant with personal belongings to ensure a safe visit.
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 Portland, ME Flight
Find answers to the most common questions about traveling from Chicago, IL to Portland, ME 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 Portland, ME, this guide helps you travel smarter and with confidence.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Portland, ME including taking a train, bus, and flight.
popular airports
Popular airports from Chicago, IL to Portland, ME
Most Chicago, IL to Portland, ME flights use the O'Hare International Airport to Portland International Jetport airport pair. Use this guide to compare Chicago, IL and Portland, ME airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Chicago
Arrival airports in Portland
Which Chicago, IL airport do flights to Portland, ME leave from?
Flights from Chicago, IL to Portland, ME 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, USA
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..
Which Portland, ME airport do flights from Chicago, IL arrive at?
Flights from Chicago, IL to Portland, ME arrive at Portland International Jetport. Portland International Jetport is 0 miles (1 km) from Portland, ME city centre.
Portland International Jetport (PWM)1001 Westbrook Street, Portland, ME 04102, USA
City-centre transport
Getting to Portland International Jetport from Portland city centre
Portland International Jetport is 1 km from Portland city centre. Public transport options include:
Bus7 · 27m · $5 · every ~2 min
7 · 30m · $5 · every ~2 min
Portland International Jetport airport facilities and services
Portland International Jetport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants available include Linda Bean's Lobster Cafe and Starbucks in the terminal.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located near the baggage claim area.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at Portland International Jetport: Parking, Taxis, WC.
Bike and car services
Available at Portland International Jetport: Car Rental.
Accessibility
Accessibility facilities are available at Portland International Jetport: Elevators, ramps.
Airports for flights from Chicago, IL to Portland, ME
See which airports are used for flights between Chicago, IL and Portland, ME, including airport details.
Flights from Chicago, IL to Portland, ME generally leave from O'Hare International Airport and arrive in Portland International Jetport.O'Hare International Airport is 2 miles (4 km) away from Chicago, IL city centre and Portland International Jetport is 0 miles (1 km) from Portland, ME city centre.
Most popular flights from Chicago, IL
More options for your journey from Chicago, IL to Portland, ME
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Most popular flights to and from Portland, ME and Chicago, IL
Most popular flights to Portland, ME
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