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Lowest round trip fares by airline from Boston and Chicago

Cheapest prices ($43 One Way, $79 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
3.5 out of 5.0
4.3 out of 5 (15 reviews)

Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ...
Travelodge by Wyndham Downtown Chicago
2.0 out of 5.0
3.1 out of 5 (9 reviews)

Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...

I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay.
Motel 6 Elk Grove Village, IL - O'Hare
2.0 out of 5.0
3.8 out of 5 (13 reviews)

Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.

Really nice and clean place. The parking lot was clear.

Flights Review

Dec 25, 2018

Pretzels could be replaced by some other snack

Nov 29, 2018

Better good

Oct 7, 2018

Nothing else.

Oct 2, 2018

Very happy with JetBlue overall experience

Sep 10, 2018

Very efficient flight. Left on time and arrived early. The pilot was communicating with the passengers on a regular basis to inform them about weather conditions. Very happy overall.

Aug 1, 2018

Disappointed flight was delayed for 5 hrs but JetBlue handled everything very nice & compensated.

Jul 18, 2018

Left on time, arrived early!!

Jul 7, 2018

Would like to have seat mounted tv

Fly From Boston to Chicago

Number of Daily Flights30
Earliest Flight Departure DateApr 23
Latest Flight Departure DateApr 23
Popular AirlinesJetBlue Airways

Cheap flights from Boston to Chicago

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.