Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

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

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Lowest round trip fares by airline from Chicago and Boston

Cheapest prices ($31 One Way, $61 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 4
ORD
Chicago
BOS
Boston
$31
Spirit Airlines
Sat, Jun 12
MDW
Chicago
BOS
Boston
$58
Delta
Wed, Aug 18 - Tue, Aug 24
ORD
Chicago
BOS
Boston
$61
Spirit Airlines
Wed, Aug 4
ORD
Chicago
BOS
Boston
$70
JetBlue Airways
Tue, Jul 13
ORD
Chicago
BOS
Boston
$79
United
Thu, Sep 23
ORD
Chicago
BOS
Boston
$79
American Airlines
Tue, Jun 8 - Tue, Jun 15
ORD
Chicago
BOS
Boston
$125
Delta
Wed, Oct 27 - Wed, Nov 3
ORD
Chicago
BOS
Boston
$139
United
Wed, Aug 18 - Tue, Aug 24
ORD
Chicago
BOS
Boston
$139
JetBlue Airways
Sat, Jun 12 - Tue, Jun 22
MDW
Chicago
BOS
Boston
$145
Delta

Great Deals On Cheap Hotels in Boston

Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave, Wakefield, MA
The price is $68 per night from May 16 to May 16
Situated on a lake, this hotel is within 9 mi (15 km) of Woburn Mall, Burlington Mall, and Saugus Town Hall. Salem Witch Museum and Tufts University are also ...
3.6/5Good! (13 reviews)
"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."

Reviewed on Oct 19, 2019

Lakeside Inn
The Constitution Inn

The Constitution Inn

2 out of 5
150 3rd Ave, Boston, MA
Get Rates
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 ...
3.3/5 (8 reviews)
"It is a very good place to go to DT,and a lot of traveler place.And is very quiet and safety."

Reviewed on Mar 3, 2020

The Constitution Inn
HI Boston

HI Boston

2 out of 5
19 Stuart Street, Boston, MA
The price is $133 per night from May 17 to May 17
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 ...
4.7/5Exceptional! (3 reviews)
"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 ..."

Reviewed on Jul 29, 2018

HI Boston
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.

Flights Review

Fly From Chicago to Boston

Origin Chicago
Destination Boston
Number of Daily Flights 35
Earliest Flight Departure Date May 21
Latest Flight Departure Date May 22
Popular Airlines JetBlue Airways

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.