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Fares from $99 One Way, $190 Round Trip from Portland to Chicago

Prices starting at $190 for return flights and $99 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.

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More About Flying To Chicago from Portland

Flights from Portland to Chicago - Frequently Asked Questions

Are there non-stop flights from Portland to Chicago?

Two airlines fly nonstop from Portland, ME Airport (PWM-Portland Intl. Jetport) to Chicago, IL Airport (ORD-O'Hare Intl.) — United Airlines and American Airlines. They'll get you where you need to go quickly and comfortably.

What is the shortest flight from Portland to Chicago?

The journey from Portland to Chicago can be as quick as 2 hours and 47 minutes. With an easy flight time like this, why not take off on an impromptu getaway?

What airlines fly from Portland to Chicago most frequently?

Consider booking a flight with United Airlines (UA), which frequently services this route. This airline offers 59 flights each month between Portland, ME Airport (PWM-Portland Intl. Jetport) and Chicago, IL Airport (ORD-O'Hare Intl.). American Airlines (AA) also operates services from Portland to Chicago. It's another excellent option and offers 23 flights every month.

Route Information for Flights from Portland to Chicago

Origin Airport IATA CodeAUG
Destination Airport IATA CodeCHI
Distance897 mi
Direct Flight AirlinesAir New Zealand, United Airlines
Earliest Flight Arrival8:48PM UTC
Latest Flight Arrival8:48PM UTC

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.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.