Cheap flights from Pittsburgh (PIT) to Chicago (CHI)

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Lowest round trip fares by airline from Pittsburgh and Chicago

Cheapest prices ($82 One Way, $164 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL, 60611
The price is $95 per night from Aug 29 to Aug 30
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
4/5 Very Good! (999 reviews)
Great affordable shared bedroom option
"Great option for a shared bedroom at a great location, very walkable, and with public transit just around the corner."

Reviewed on Aug 9, 2022

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL, 60605
The price is $129 per night from Aug 28 to Aug 29
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in ...
3.1/5 (1,105 reviews)
👌 water pressure
"This the second time I've stayed at this poticular location. I've always been impressed with the service, cleaniness, and oh! The shower!! 👌👌 Best water pressure I've ever used in a hotel (heck, it was better then my water pressure back home!)"

Reviewed on Aug 12, 2022

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL, 60007
The price is $55 per night from Sep 5 to Sep 6
Stay at this business-friendly motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
4/5 Very Good! (1,000 reviews)
"It's not that bad for the price I paid. Spacious room, small bathroom, super hard bed."

Reviewed on Aug 13, 2022

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Pittsburgh to Chicago

Origin Pittsburgh
Destination Chicago
Number of Daily Flights 36
Earliest Flight Departure Date Aug 23
Latest Flight Departure Date Aug 23
Popular Airlines United Airlines

Cheap flights from Pittsburgh to Chicago

Pittsburgh International Airport (PIT) is located almost 20 miles northwest of Pittsburgh, PA. Driving to PIT from Pittsburgh takes about 30 minutes via I-376 W and the 28X Airport Flyer is a convenient public transportation solution.

Typical flight times to Chicago O’Hare International Airport (ORD) are just over an hour. Taxis are located on the lower-level curb front area next to the baggage claim and free shuttles to all rental car companies are located outside baggage claim as well. Regional buses also offer rides to further destinations outside of the greater Chicago area.

Attractions and Tips

Chicago is the cosmopolitan epicenter of America's Midwest. Located in Grant Park, the Art Institute of Chicago is an internationally celebrated must. The Briar Street Theatre, home of the popular performers the Blue Man Group, is just a 30 minute drive from ORD. Enjoy Zagat rated cuisine from Bistro Bordeaux to Ada Street, as well as Chicago's famed deep dish pizza at Giordano's and many other pizza joints.

Chicago’s weather varies from frigid extremes in winter to pleasantly warm in the summer. Visitors who travel during winter should be extra careful to check the status of flights that may be hindered due to snow, rain or ice. When choosing a hotel, explore the whole city; many neighborhoods have boutique and large chain establishments alike.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.