Cheap flights from Boston (BOS) to Chicago (CHI)

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Lowest round trip fares by airline from Boston and Chicago

Cheapest prices ($64 One Way, $144 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 $106 per night from Jun 27 to Jun 28
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 ...
3.9/5 Good! (9 reviews)
"I really appreciated the staff there. Thanks"

Reviewed on Oct 16, 2021

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 $116 per night from May 30 to May 31
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and onsite parking. Our guests praise the breakfast and the restaurant in our reviews. ...
3.4/5 Good! (9 reviews)
"Friendly staff, conveniently located, great value!"

Reviewed on Oct 5, 2021

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 $45 per night from Jun 27 to Jun 28
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 ...
4.1/5 Very Good! (12 reviews)
"This was a very great bang for your buck! Clean and Quiet"

Reviewed on Sep 11, 2021

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 Boston to Chicago

Origin Boston
Destination Chicago
Number of Daily Flights 71
Earliest Flight Departure Date Jun 5
Latest Flight Departure Date Jun 6
Popular Airlines American Airlines

Find cheap tickets for flights from Boston to Chicago at CheapTickets. Why shop around when the low fares are handed to you?

Logan International Airport (BOS) is presently the only airport with bargain commercial Boston to Chicago flights via American Airlines. A 12-year top-to-bottom update project by Massachusetts Port Authority (Massport) was concluded only six years ago. Passengers departing on domestic flights from Boston to Chicago will most likely notice the parking garage, terminals, and arrival and departure roadway improvements. American Airlines operates an Admirals Club in Terminal B North for passengers waiting to board budget Boston to Chicago flights, which usually depart from Gates B22-36. Logan strives to improve the customer experience, and has been noted for the variety of choices available for arrival and departure transport, and its on-time departure record.

O'Hare International Airport (ORD) and Midway International Airport (MDW) both receive incoming low cost flights from Boston to Chicago. Discount carriers JetBlue Airways and Spirit Airlines share gate 3L with American Airlines, which also utilizes Gates 3H and 3K. United Airlines and their affiliate United Express and subcontractor Shuttle America keep to Gates 1B and 1C. Southwest Airlines Boston to Chicago flights arrive at Midway's A and B concourses. Travelers exiting Midway enjoy convenient access to the central business district and Loop through Stevenson Expressway and Chicago Transit Authority's (CTA) Orange Line elevated trains. CTA also uses the Midway station for bus service to several stops in the vicinity.

*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.