- 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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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, July 31. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
 AA2970+ AA6124 | 5:00 AM O'Hare International Airport | 4h31 | 10:31 AM Portland International Jetport | 1 transfer | |
 UA2666 · UA1598 | 5:00 AM O'Hare International Airport | 9h49 | 3:49 PM Portland International Jetport | 1 transfer | |
| AA2842 · AA2348 | 5:07 AM O'Hare International Airport | 7h33 | 1:40 PM Portland International Jetport | 1 transfer | |
AA344+ AA4339 | 5:58 AM O'Hare International Airport | 5h13 | 12:11 PM Portland International Jetport | 1 transfer | |
| AA327 · AA2931 | 6:00 AM O'Hare International Airport | 5h35 | 12:35 PM Portland International Jetport | 1 transfer | |
| UA2806 · UA1598 | 6:00 AM O'Hare International Airport | 8h49 | 3:49 PM Portland International Jetport | 1 transfer | |
 B61206 · B6508 | 6:00 AM O'Hare International Airport | 7h24 | 2:24 PM Portland International Jetport | 1 transfer | |
| AA1784 · AA2348 | 6:30 AM O'Hare International Airport | 6h10 | 1:40 PM Portland International Jetport | 1 transfer | |
| AA2115 · AA2354 | 6:37 AM O'Hare International Airport | 6h39 | 2:16 PM Portland International Jetport | 1 transfer | |
| AA2723 · AA2931 | 7:00 AM O'Hare International Airport | 4h35 | 12:35 PM Portland International Jetport | 1 transfer | |
| UA2232 · UA1637 · UA3599 | 7:00 AM O'Hare International Airport | 10h29 | 6:29 PM Portland International Jetport | 2 transfers | |
| AA2965 · AA344 | 7:02 AM O'Hare International Airport | 4h09 | 12:11 PM Portland International Jetport | 1 transfer | |
| UA1217 · UA1598 | 7:05 AM O'Hare International Airport | 7h44 | 3:49 PM Portland International Jetport | 1 transfer | |
| UA563 · UA3685 | 7:10 AM O'Hare International Airport | 5h15 | 1:25 PM Portland International Jetport | 1 transfer | |
| AA2345 · AA2355 | 8:00 AM O'Hare International Airport | 7h36 | 4:36 PM Portland International Jetport | 1 transfer | |
| AA3222 · AA2352 | 8:00 AM O'Hare International Airport | 8h09 | 5:09 PM Portland International Jetport | 1 transfer | |
| AA4488 | 8:00 AM O'Hare International Airport | 2h37 | 11:37 AM Portland International Jetport | 0 transfersDirect | |
| AA471 · AA2354 | 8:29 AM O'Hare International Airport | 4h47 | 2:16 PM Portland International Jetport | 1 transfer | |
| AA1555 · AA2353 | 8:30 AM O'Hare International Airport | 7h11 | 4:41 PM Portland International Jetport | 1 transfer | |
| UA2277 · UA3535 | 8:40 AM O'Hare International Airport | 4h54 | 2:34 PM Portland International Jetport | 1 transfer | |
| AA2530 · AA2352 | 9:00 AM O'Hare International Airport | 7h09 | 5:09 PM Portland International Jetport | 1 transfer | |
| B6906 · B6308 | 9:42 AM O'Hare International Airport | 13h39 | 12:21 AM Portland International Jetport | 1 transfer | |
| AA2398 · AA2355 | 9:42 AM O'Hare International Airport | 5h54 | 4:36 PM Portland International Jetport | 1 transfer | |
| UA2684 · UA555 · UA3627 | 10:29 AM O'Hare International Airport | 12h01 | 11:30 PM Portland International Jetport | 2 transfers | |
| AA2355+AA4809 | 10:45 AM O'Hare International Airport | 4h51 | 4:36 PM Portland International Jetport | 1 transfer | |
| UA5756 · UA6190 · UA3651 | 10:50 AM O'Hare International Airport | 7h37 | 7:27 PM Portland International Jetport | 2 transfers | |
| UA2804 | 11:00 AM O'Hare International Airport | 2h31 | 2:31 PM Portland International Jetport | 0 transfersDirect | |
| UA1869 · UA1831 · UA3627 | 11:07 AM O'Hare International Airport | 11h23 | 11:30 PM Portland International Jetport | 2 transfers | |
| AA1743+AA6125 | 11:40 AM O'Hare International Airport | 5h54 | 6:34 PM Portland International Jetport | 1 transfer | |
| UA606 · UA3599 | 12:11 PM O'Hare International Airport | 5h18 | 6:29 PM Portland International Jetport | 1 transfer | |
| AA3280 · AA2120 | 1:17 PM O'Hare International Airport | 8h19 | 10:36 PM Portland International Jetport | 1 transfer | |
AA1675+ AA5233 | 1:20 PM O'Hare International Airport | 9h39 | 11:59 PM Portland International Jetport | 1 transfer | |
| UA2794 · UA1831 · UA3627 | 1:30 PM O'Hare International Airport | 9h00 | 11:30 PM Portland International Jetport | 2 transfers | |
| UA1314 · UA4180 · UA3627 | 2:00 PM O'Hare International Airport | 8h30 | 11:30 PM Portland International Jetport | 2 transfers | |
| UA1502 · UA3633 · UA3627 | 2:20 PM O'Hare International Airport | 8h10 | 11:30 PM Portland International Jetport | 2 transfers | |
| UA1502 · UA554 · UA3627 | 2:20 PM O'Hare International Airport | 8h10 | 11:30 PM Portland International Jetport | 2 transfers | |
| UA1349 · UA3578 · UA3627 | 2:25 PM O'Hare International Airport | 8h05 | 11:30 PM Portland International Jetport | 2 transfers | |
| UA1349 · UA3565 · UA3627 | 2:25 PM O'Hare International Airport | 8h05 | 11:30 PM Portland International Jetport | 2 transfers | |
| AA2769+AA5233 | 2:55 PM O'Hare International Airport | 8h04 | 11:59 PM Portland International Jetport | 1 transfer | |
| UA5867 · UA6362 · UA2064 | 3:00 PM O'Hare International Airport | 7h51 | 11:51 PM Portland International Jetport | 2 transfers | |
| AA4774 | 3:18 PM O'Hare International Airport | 2h34 | 6:52 PM Portland International Jetport | 0 transfersDirect | |
| AA2819 · AA1889 | 3:29 PM O'Hare International Airport | 6h04 | 10:33 PM Portland International Jetport | 1 transfer | |
| UA5638 · UA554 · UA3627 | 3:50 PM O'Hare International Airport | 6h40 | 11:30 PM Portland International Jetport | 2 transfers | |
| UA2437 · UA2064 | 3:53 PM O'Hare International Airport | 6h58 | 11:51 PM Portland International Jetport | 1 transfer | |
| UA5954 · UA6362 · UA2064 | 3:59 PM O'Hare International Airport | 6h52 | 11:51 PM Portland International Jetport | 2 transfers | |
| UA485 · UA3627 | 4:31 PM O'Hare International Airport | 5h59 | 11:30 PM Portland International Jetport | 1 transfer | |
| AA1848 · AA1889 | 5:07 PM O'Hare International Airport | 4h26 | 10:33 PM Portland International Jetport | 1 transfer | |
| B6406 · B6308 | 5:27 PM O'Hare International Airport | 5h54 | 12:21 AM Portland International Jetport | 1 transfer | |
| UA1954 · UA726 | 5:45 PM O'Hare International Airport | 19h35 | 2:20 PM Portland International Jetport | 1 transfer | |
| AA1787+AA5233 | 5:55 PM O'Hare International Airport | 5h04 | 11:59 PM Portland International Jetport | 1 transfer | |
| UA1401 | 6:08 PM O'Hare International Airport | 2h33 | 9:41 PM Portland International Jetport | 0 transfersDirect | |
| UA2202 · UA2064 | 6:12 PM O'Hare International Airport | 4h39 | 11:51 PM Portland International Jetport | 1 transfer | |
| UA1475 · UA726 | 6:29 PM O'Hare International Airport | 18h51 | 2:20 PM Portland International Jetport | 1 transfer | |
| UA2813 · UA726 | 8:02 PM O'Hare International Airport | 17h18 | 2:20 PM Portland International Jetport | 1 transfer | |
| AA4403 | 9:09 PM O'Hare International Airport | 2h34 | 12:43 AM Portland International Jetport | 0 transfersDirect | |
Find all the dates and times for this journey
Airlines: Republic Airlines from Chicago, IL to Portland, MEFind the best flights between Chicago, IL to Portland, ME with Omio's travel partners Republic Airlines from $111 (€90). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
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
Republic Airlines frequency
2 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.
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.
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.
Cheap plane tickets from Chicago, IL to Portland, ME can start from as little as $159 (€130) when you book in advance. The average flight ticket price for Chicago, IL to Portland, ME is $187 (€152) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Chicago, IL to Portland, ME is 2h 38m to travel the 889 miles (1432 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
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 3 direct flights a day from Chicago, IL to Portland, ME with Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Chicago, IL to Portland, ME, you can count on Republic 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.
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 1 miles (3 km) away from Chicago, IL city centre and Portland International Jetport is 0 miles (1 km) from Portland, ME city centre.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Portland, ME including taking a bus, train, and flight.
For domestic flights we recommend to arrive 1.5 to 2 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.
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.
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.
More options for your journey from Chicago, IL to Portland, ME
Here are some other resources that might have the information you need
Most popular flights to and from Portland, ME and Chicago, IL
Most popular flights to Portland, ME
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