Chicago, IL CHI to Portland, ME PWM flight with Republic Airlines

Sat, Dec 13
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Republic Airlines
Sky West Airlines
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Republic Airlines
Sky West Airlines
Ryanair
Vueling Airlines
KM Malta Airlines
1,000+ travel companies
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Journey information

Overview: Chicago, IL to Portland, ME flight

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Flights from Chicago, IL to Portland, ME depart on average 22 times per day, taking around 2h 27m. Cheap flight tickets for this journey start at $135 (€107) but you can travel from only $118 (€94) by bus.

There are 1 flights per day. The earliest flight runs at 05:00, the last at 21:30. The fastest flight covers the 889 miles (1432 km) distance in 5h 23m. 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 $118 (€94)
Distance
889 miles (1432 km)
Average flight duration
2h 27m
Cheapest ticket price
$135 (€107)
Flights per day
22
Direct flights
1
Fastest flight
5h 23m
Cheapest month to travel
August
First flight
05:00
Last flight
21:30
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 $118 (€94)

The cheapest and fastest flights from Chicago, IL to Portland, ME

Showing times and prices for Dec 17

Cheapest price

$135

Average price

$135

Fastest journey

5 h 23 m

Average duration

5 h 23 m

Flights per day

1

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 $135 if you buy it on the day, but the cheapest tickets can be found for only $135.

Fast flights

Of the 1 flights that leave Chicago, IL for Portland, ME onWed, Dec 17, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Wed, Dec 17 the direct flights cover the 1432 km distance in an average of 5 h 23 m but if you time it right, some flights will get you there in just 5 h 23 m .

On Wed, Dec 17 the longest flights will take 5 h 23 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.

American Airlines
10:21PM5h23
Chicago, IL
03:44AMPortland, ME
$1351One-way
0 transfers

Travel Information

Compare bus and flight for Chicago, IL to Portland, ME

Omio recommends booking the flight as it is the most popular option from Chicago, IL to Portland, ME among Omio's users. If you are prioritising price take the bus with prices starting from €94. For those with little time consider booking a flight which can get you there in 2h 27m. The ticket price range depends on the travel mode: a bus costs an average of €94, and a flight costs an average of €107.

Distance: 889 miles (1432 km)

Compare flight with

Most popular
Flight
Bus

€107

Average price

€94

Average price

Cheapest

5h 27m

Average total duration

Fastest

2h 27m

Onboard

+

3h 0m

Additional time*

28h 20m

Average total duration

27h 50m

Onboard

+

30m

Additional time*

Sky West Airlines

Most popular airline

Greyhound

Most popular bus company

Direct Options

Direct Options

Live departures

Chicago, IL to Portland, ME flight times

The table below shows live departures for Chicago, IL to Portland, ME flights for tomorrow, Wednesday, December 17. You can also manually refresh the results below to see updated flight journeys.

Last updated at 11:01 PM
ProviderDepartsDurationArrivesTransfers
Tickets
american_airlines10:21 PM Chicago, IL
5h23
3:44 AM Portland, ME0 transfersDirect

This is the last flight of the day.

Find all the dates and times for this journey

Compare prices and tickets Chicago, IL to Portland, ME by bus or flight

Compare 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.

Wed
Dec 17
Thu
Dec 18
Fri
Dec 19
Sat
Dec 20
Sun
Dec 21
Mon
Dec 22
Tue
Dec 23

Airlines: Republic Airlines, Sky West Airlines from Chicago, IL to Portland, MEFind the best flights between Chicago, IL to Portland, ME with Omio's travel partners Republic Airlines, Sky West Airlines from $118 (€94). We can find you the best deals, schedules and tickets when comparing and booking the best trip.

Sky West 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
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.
Motorbike

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
1 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
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: 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.

FAQs
Cheap plane tickets from Chicago, IL to Portland, ME can start from as little as $150 (€120) when you book in advance. The average flight ticket price for Chicago, IL to Portland, ME is $250 (€200); 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 2 h 28 min   to travel the 887 mile (1431 km) long trip, with around there are 27 flights per day. Journey times can vary on weekends and holidays.
The earliest flight from Chicago, IL to Portland, ME leaves at 5: 00AM. Plan your trip with the Journey Planner   from Omio.
The latest flight from Chicago, IL to Portland, ME leaves at 9: 01PM.
There are 27 flights a day from Chicago, IL to Portland, ME which require at least one change with United. Schedules can vary on holidays or weekends with fewer flights.
Take the Chicago, IL to Portland, ME flight with United. However, it's always good to check out all possible airlines for the route from Chicago, IL to Portland, ME as there might be differences in the amenities they offer.
The cheapest month for a flight from Chicago, IL to Portland, ME is August.
You have options as you can travel between Chicago, IL and Portland, ME 3 different ways: bus, train or flight.
Since neither Chicago, IL nor Portland, ME are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. 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 Chicago, IL and Portland, ME all year round.
The best events to attend in Portland, ME include:
  • Portland Rose Festival, a vibrant celebration of roses featuring parades, carnival rides, and cultural events
  • Portland International Beer Fest, a lively festival showcasing craft beers from around the world with tastings and food pairings
  • Waterfront Blues Festival, an annual music event featuring top blues artists and benefiting local charities.
The best holidays to experience in Portland, ME include:
  • Independence Day, vibrant fireworks and festive celebrations throughout the city
  • Labor Day, pleasant weather perfect for outdoor activities and local events
  • Thanksgiving, a time for family gatherings with a cozy atmosphere and fewer crowds.
The best seasons to visit Portland, ME are Spring or Summer. The best weather to explore Portland, ME is during June-August or September-October.
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.

popular airports

Popular airports from Chicago, IL to Portland, ME

Chicago
Portland
The major airport for departures 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 trip from Chicago to Portland.
Amenities at airport
WifiWifi
ShoppingShopping
ParkingParking
DiningDining
ATMATM
TaxisTaxis
AccessibilityAccessibility
WCWC
HotelHotel
ShowerShower
LoungeLounge
Lost and Found OfficeLost and Found Office
Car RentalCar Rental
information
ticketOfficeHours
Distance to city center
3 km
carConnection
Car connection
I-190, Exit 1
Wifi
Wifi
  • Free Wi-Fi available throughout the airport.
Shopping
Shopping
  • Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
Parking
  • Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
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
Taxis
  • Available outside the terminal.
Accessibility
Accessibility
  • Elevators, ramps, toilets
WC
WC
  • Available throughout the airport.
Hotel
Hotel
  • Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
Shower
  • Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
Lounge
  • Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
Lost and Found Office
  • Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
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 Chicago, IL to Portland, ME

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Most popular flights to and from Portland, ME and Chicago, IL

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