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Lowest round trip fares by airline from Chicago and Boston

Cheapest prices ($19 One Way, $37 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Boston

Lakeside Inn
2.0 out of 5.0
3.2 out of 5 (19 reviews)

Situated on a lake, this hotel is 3.1 mi (5 km) from Woburn Mall and within 12 mi (20 km) of Burlington Mall and Salem Witch Museum. Tufts University and Revere ...

Old Hotel but clean. small room. Breakfast was good. No clock radio in room but they did give us one. Phone not working properly.Nick the night clerk was very friendly and helpful.All in all it was a pretty good stay. Just wish the room was bigger so they could add a small refrigerator.
The Constitution Inn
2.0 out of 5.0
3.2 out of 5 (8 reviews)

Located in Charlestown, this hotel is within a 10-minute walk of The Freedom Trail and USS Constitution Museum. TD Garden and Bunker Hill Monument are also within ...

It is a very good place to go to DT,and a lot of traveler place.And is very quiet and safety.
HI Boston
2.0 out of 5.0
4.7 out of 5 (3 reviews)

Located in Theatre District, this eco-friendly hostel is within a 5-minute walk of Cutler Majestic Theatre and Boston Opera House. Boston Common and Boston Public ...

I liked that the hostel was close to downtown Boston and public transportation. It was a cheap place to stay and a great place to meet people. I am not used to bunk beds, but it wasn't too bad. You have to be considerate of other people in the room and not have the big light on when other people ...

Flights Review

Feb 4, 2020

Very happy

Dec 3, 2019

Pilot flew safely in bad weather.

Nov 3, 2018

Was a really great experience for my first time ever flying.

Oct 21, 2018

Sit space is too tight.

Oct 8, 2018

Don the head purser was very helpful and ran a great show on my flight.

Aug 19, 2018

Quite simply, it was a very comfortable flight.

Aug 2, 2018

Flight delayed and we sat on the plane for 1.5 hrs before take off

Jul 7, 2018

I’m very upset about my return flight to Boston! My flight was cancelled rescheduled for 5 pm I was at airport expecting to get on my 7:10 flight nobody informed me we had to take a 100$ Uber to a different airport to be able to get home!

Feb 7, 2018

Despite having a rather lengthy delay after boarding the plane, once we got going it was great. During the delay, the pilot communicated with us and kept us aware if what was going on.

Fly From Chicago to Boston

Number of Daily Flights24
Earliest Flight Departure DateJul 11
Latest Flight Departure DateJul 11
Popular AirlinesSpirit Airlines

Cheap flights from Chicago to Boston

Cheap flights from Chicago to Boston

Get away from The Windy City and explore a cultural mecca in New England, when you fly from Chicago to Boston. The city draws in both vacationers and those attending to business. Once you arrive at General Edward Lawrence Logan International Airport (BOS,) head to the nearby Seaport District and explore modern masterpieces at The Institute of Contemporary Art Boston. A great way to tour The Walking City is to stroll through the historic Boston Common Park, or to follow the marked paths of the Rose Fitzgerald Kennedy Greenway.

Key Facts

U.S. Route 1 runs through the heart of Boston and offers convenient access to neighboring communities like Quincy and Lynn. You can also navigate downtown Boston by driving on I-90. When using these highways, look for the exits towards Fenway Park and TD Garden, in order to reach Boston's premier sports venues. Head to Faneuil Hall and shop for some souvenirs in a marketplace that has been in business since colonial times. Take an elevator to the top of Prudential Tower to observe Boston's skyline from more than 700 feet above ground.

Hints and Tips

The flight from O'Hare International Airport (ORD) to General Edward Lawrence Logan International Airport takes two and a half hours. Once you get a rental vehicle at BOS, you'll be a short drive away from historic sites in the North End, like The Paul Revere House and other landmarks along the Freedom Trail.

*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.