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

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Lowest round trip fares by airline from Boston and Chicago

Cheapest prices ($44 One Way, $88 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
The price is $99 per night from Oct 17 to Oct 18
$99
per night
Oct 17 - Oct 18
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the property condition in our reviews. ...
7.8/10 Good! (1,003 reviews)
"Really cute stay close to everything! I would recommend the premium kind room"

Reviewed on Sep 25, 2023

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $118 per night from Oct 9 to Oct 10
$118
per night
Oct 9 - Oct 10
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the spacious rooms in our reviews. Popular attractions ...
6.2/10 (1,447 reviews)
"I was just visiting passing through to see a friend so I decided to stay for a night, hotel is ok to be honest opinion"

Reviewed on Sep 26, 2023

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
The price is $60 per night from Oct 2 to Oct 3
$60
per night
Oct 2 - Oct 3
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Allstate Arena and Wolff's Flea Market ...
8/10 Very Good! (1,001 reviews)
"Great location, good price"

Reviewed on Sep 24, 2023

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
64
Earliest Flight Departure Date
Oct 4
Latest Flight Departure Date
Oct 5
Popular Airlines
JetBlue Airways

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.