$83 Cheap flight deals from Portland (PWM) to Chicago (CHI)

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This Weekend's Flight Deals from Portland to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $83 One Way, $176 Round Trip from Portland to Chicago

Prices starting at $176 for return flights and $83 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Chicago from Portland

Route Information for Flights from Portland to Chicago

Origin Airport IATA Code
PWM
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Finding Flights from Portland to Chicago

Portland, ME, Airport Information

Searching for low-cost flights from Portland, ME, can be a challenging task when searching through several airlines' websites. Orbitz.com can save you time and money by comparing these rates simultaneously, allowing you to choose the rate that suits your budget and needs. The major air service provider for the Portland area is the Portland International Jetport. It is located at 1001 Westbrook Street and is about a 10-minute drive from downtown Portland. The airport is served by several airlines, including Air Canada, Air Tran, Delta, jetBlue, United, US Airways, and Twin Cities Air Service. Orbitz.com will compare the fares of these airlines so you can choose the best rate.

Airport Parking Information

The airport has long-term and short-term parking lots, including a five-story garage located within walking distance of the terminals. The hourly parking rate is $2 per hour with a maximum daily rate of $48; long-term rates are $12 a day.

Transportation to the Airport

Transportation to the airport is available by taxi, car rental, public transportation, and limousine service. A taxi fare from downtown to the airport will cost about $17, and payment can be made by cash or major credit card. Alamo, Avis, Enterprise, Hertz, and National are the car rental companies available at the airport. Orbitz.com will search these companies for sales and discounts, providing you the best rate for your budget.

Airport Restaurant Information

The airport is home to a few restaurants, including Café Stroudwater, Gladieux Corp, and the Epicurean Feast. All these restaurants have a wide variety of menu items available to satisfy everyone. Check with Orbitz.com for the best rates on flights from Portland to save time and money.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Are there non-stop flights from Portland to Chicago?
There sure are, which is fantastic news if you’re not a big fan of layovers. United Airlines and American Airlines fly straight from Portland Intl. Jetport Airport (PWM) to O’Hare Airport.
What is the shortest flight from Portland to Chicago?
The shortest flight from Portland Intl. Jetport to Midway Intl. Airport (MDW) is 3 hours and 18 minutes. Bring something extra to help pass the time, like a fascinating read or a portable board game.
What airlines fly from Portland to Chicago most frequently?
Look up United Airlines (UA). This airline offers some of the most frequent flights from Portland, ME (PWM-Portland Intl. Jetport) to O’Hare Airport. It operates 91 services on this route each month and is popular with passengers. American Airlines (AA) will also fly you to your destination in style and comfort. Offering 78 flights per month between Portland and Chicago, it’s another popular airline to look into.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.