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Journey information
Overview: Portland, ME to Chicago, IL flight
USAUSA
Flights from Portland, ME to Chicago, IL depart on average 28 times per day, taking around 2h 53m. Cheap flight tickets for this journey start at $508 (€406) but you can travel from only $289 (€231) by bus.
There are 2 flights per day. The earliest flight runs at 05:00, the last at 22:05. The fastest flight covers the 889 miles (1432 km) distance in 3h 12m. August 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 $289 (€231)
Distance 889 miles (1432 km) |
Average flight duration 2h 53m |
Cheapest ticket price $508 (€406) |
Flights per day 28 |
Direct flights 2 |
Fastest flight 3h 12m |
Cheapest month August |
First flight 5:00 AM |
Last flight 10:05 PM |
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 $289 (€231)
Travel Information
Compare bus, train, and flight for Portland, ME to Chicago, IL
Omio recommends booking the train as it is the most popular option from Portland, ME to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $289. For those with little time consider booking a flight which can get you there in 2h 53m. The ticket price range depends on the travel mode: a bus costs an average of $289, and a flight costs an average of $508.
Distance: 889 miles (1432 km)
Compare flight with
| Flight | Most popular Train | Bus |
|---|---|---|
$530 Average price | $471 Average price | $308 Average price Cheapest |
5h 53m Average total duration Fastest 2h 53m Onboard + 3h 0m Additional time* | 24h 49m Average total duration 24h 19m Onboard + 30m Additional time* | 27h 5m Average total duration 26h 35m Onboard + 30m Additional time* |
 Most popular airline |  Most popular train company |  Most popular bus company |
Direct Options | Direct Options | Direct Options |
Live departures
Portland, ME to Chicago, IL flight times
The table below shows live departures for Portland, ME to Chicago, IL flights for today, Sunday, April 12. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
 AA2610 · AA3307 | 2:47 PM Portland International Jetport | 6h58 | 9:45 PM O'Hare International Airport | 1 transfer | |
| AA2610 · AA1328 | 2:47 PM Portland International Jetport | 11h34 | 2:21 AM O'Hare International Airport | 1 transfer | |
| AA2610+AA4484 | 2:47 PM Portland International Jetport | 9h21 | 12:08 AM O'Hare International Airport | 1 transfer | |
 AA6124+AA1312 | 2:50 PM Portland International Jetport | 11h45 | 2:35 AM O'Hare International Airport | 1 transfer | |
| AA6124+AA3331 | 2:50 PM Portland International Jetport | 13h44 | 4:34 AM O'Hare International Airport | 1 transfer | |
| AA6124+AA490 | 2:50 PM Portland International Jetport | 9h10 | 12:00 AM O'Hare International Airport | 1 transfer | |
 UA4477 · UA1168 | 3:09 PM Portland International Jetport | 5h55 | 9:04 PM O'Hare International Airport | 1 transfer | |
| UA4477 · UA661 | 3:09 PM Portland International Jetport | 8h21 | 11:30 PM O'Hare International Airport | 1 transfer | |
| UA4477 · UA788 | 3:09 PM Portland International Jetport | 6h47 | 9:56 PM O'Hare International Airport | 1 transfer | |
| AA1008 · AA1452 | 3:57 PM Portland International Jetport | 5h24 | 9:21 PM O'Hare International Airport | 1 transfer | |
| AA1008 · AA2530 | 3:57 PM Portland International Jetport | 7h01 | 10:58 PM O'Hare International Airport | 1 transfer | |
| UA4481 · UA1738 | 6:12 PM Portland International Jetport | 10h31 | 4:43 AM O'Hare International Airport | 1 transfer | |
| UA4481 · UA4042 · UA686 | 6:12 PM Portland International Jetport | 8h53 | 3:05 AM O'Hare International Airport | 2 transfers | |
| UA4481 · UA4042 · UA349 | 6:12 PM Portland International Jetport | 7h53 | 2:05 AM O'Hare International Airport | 2 transfers | |
| UA4481 · UA4042 · UA366 | 6:12 PM Portland International Jetport | 9h48 | 4:00 AM O'Hare International Airport | 2 transfers | |
| UA4481 · UA1831 · UA1206 | 6:12 PM Portland International Jetport | 10h25 | 4:37 AM O'Hare International Airport | 2 transfers | |
| UA4481 · UA2497 | 6:12 PM Portland International Jetport | 5h32 | 11:44 PM O'Hare International Airport | 1 transfer | |
| AA6123+AA3331 | 7:02 PM Portland International Jetport | 9h32 | 4:34 AM O'Hare International Airport | 1 transfer | |
| AA6123+AA1312 | 7:02 PM Portland International Jetport | 7h33 | 2:35 AM O'Hare International Airport | 1 transfer | |
| UA4496 · UA254 | 7:22 PM Portland International Jetport | 6h15 | 1:37 AM O'Hare International Airport | 1 transfer | |
| UA4496 · UA546 | 7:22 PM Portland International Jetport | 7h11 | 2:33 AM O'Hare International Airport | 1 transfer | |
| UA4496 · UA1206 | 7:22 PM Portland International Jetport | 9h15 | 4:37 AM O'Hare International Airport | 1 transfer | |
| UA3551 | 8:28 PM Portland International Jetport | 3h10 | 11:38 PM O'Hare International Airport | 0 transfersDirect | |
 AA3474 | 10:01 PM Portland International Jetport | 3h13 | 1:14 AM O'Hare International Airport | 0 transfersDirect | |
| UA6013 | 10:33 PM Portland International Jetport | 3h10 | 1:43 AM O'Hare International Airport | 0 transfersDirect | |
| UA4572 · UA1206 | 11:15 PM Portland International Jetport | 5h22 | 4:37 AM O'Hare International Airport | 1 transfer | |
| AA6125+AA2095 | 11:23 PM Portland International Jetport | 14h31 | 1:54 PM O'Hare International Airport | 1 transfer | |
| AA6125+AA2006 | 11:23 PM Portland International Jetport | 13h16 | 12:39 PM O'Hare International Airport | 1 transfer | |
| AA6125+AA3331 | 11:23 PM Portland International Jetport | 5h11 | 4:34 AM O'Hare International Airport | 1 transfer | |
| UA4296 · UA1738 | 11:36 PM Portland International Jetport | 5h07 | 4:43 AM O'Hare International Airport | 1 transfer | |
| UA4296 · UA1252 | 11:36 PM Portland International Jetport | 16h51 | 4:27 PM O'Hare International Airport | 1 transfer | |
| UA4296 · UA279 | 11:36 PM Portland International Jetport | 12h50 | 12:26 PM O'Hare International Airport | 1 transfer | |
| UA4296 · UA1775 | 11:36 PM Portland International Jetport | 15h02 | 2:38 PM O'Hare International Airport | 1 transfer | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Portland, ME to Chicago, IL by bus, train, or flight
Compare bus, train, 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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Airlines: Republic Airlines from Portland, ME to Chicago, ILFind the best flights between Portland, ME to Chicago, IL with Omio's travel partners Republic Airlines from $289 (€231). 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
Average Duration
3h 1m
Cheapest Price
$116 (€93)
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.
FAQs: Portland, ME to Chicago, IL Flight
Find answers to the most common questions about traveling from Portland, ME to Chicago, IL 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 Chicago, IL, this guide helps you travel smarter and with confidence.
Cheap plane tickets from Portland, ME to Chicago, IL can start from as little as $508 (€406) when you book in advance. The average flight ticket price for Portland, ME to Chicago, IL is $530 (€424) ; 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 Portland, ME to Chicago, IL is 3h 12m 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 Portland, ME to Chicago, IL leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Portland, ME to Chicago, IL leaves at 10:05 PM.
Yes, there are 2 direct flights a day from Portland, ME to Chicago, IL with Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Portland, ME to Chicago, IL, you can count on Republic Airlines for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service between Portland, ME and Chicago, IL and compare the amenities they offer before buying a plane ticket.
Flights from Portland, ME to Chicago, IL generally leave from Portland International Jetport and arrive in O'Hare International Airport.Portland International Jetport is 0 miles (1 km) away from Portland, ME city centre and O'Hare International Airport is 1 miles (3 km) from Chicago, IL city centre.
The cheapest month for a flight from Portland, ME to Chicago, IL is August.
It's helpful to compare your options as there are 3 ways to travel between Portland, ME and Chicago, IL including taking a bus, train, and flight.
Since neither Portland, ME nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is a time difference of 1 h between Portland, ME and Chicago, IL all year round.
The best events to attend in Chicago, IL include:
- Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
- Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
- Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
The best holidays to experience in Chicago, IL include:
- Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
- Independence Day, spectacular fireworks and festive celebrations throughout the city
- Labor Day, a lively atmosphere with various festivals and pleasant weather.
The best things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
The best season to visit Chicago, IL is Spring or Summer. The best weather to explore Chicago, IL is during May-September.
We recommend using the train as it is the most popular way to get from Portland, ME to Chicago, IL among Omio's users.
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 Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
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 Portland, ME to Chicago, IL
Portland
Chicago
The major airport for departures in Portland is Portland International Jetport. Find all the information you need to know about services, amenities and connections at Portland International Jetport for your trip from Portland to Chicago.
Amenities at airport
Wifi
Shopping
Parking
Dining
ATM
Taxis
Accessibility
WC
Lounge
Lost and Found Office
Car Rentalinformation
Distance to city center
1 km
Car connection
I-95, Exit 46Wifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops include Paradies Lagardère and Hudson News in the terminal.
Parking
- Parking available near terminals, approximately 0.47€ ($0.50) per hour.
Dining
- Restaurants available include Linda Bean's Lobster Cafe and Starbucks in the terminal.
Taxis
- Available outside the terminal.
Accessibility
- Elevators, ramps
WC
- Available throughout the airport.
Lounge
- Lounge access available for Delta Sky Club members.
Lost and Found Office
- Lost and Found located in the main terminal.
Car Rental
- Car rental services are available from companies like Avis, Budget, and Hertz on-site.
Public transit options for Portland International Jetport
- Bus Route 5, Portland Transportation Center, 3 miles
The major airport for arrivals in Chicago is O'Hare International Airport. Find all the information you need to know about services, amenities and connections at O'Hare International Airport for your journey to Chicago from Portland.
Amenities at airport
WifiShoppingParkingDiningATMTaxisAccessibilityWC
Hotel
ShowerLoungeLost and Found OfficeCar Rentalinformation
Distance to city center
3 kmCar connection
I-190, Exit 1Wifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Taxis
- Available outside the terminal.
Accessibility
- Elevators, ramps, toilets
WC
- Available throughout the airport.
Hotel
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
- Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
- Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
Public transit options for O'Hare International Airport
- CTA Blue Line, O'Hare Station, 45 minutes to city center
More options for your journey from Portland, ME to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Portland, ME
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