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

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Lowest round trip fares by airline from Chicago and Boston

Cheapest prices ($75 One Way, $128 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

Lakeside Inn

2 out of 5
595 North Ave, Wakefield, MA, 01880
The price is $99 per night from May 23 to May 24
Stay at this business-friendly hotel in Wakefield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
3.5/5 Good! (8 reviews)

Reviewed on Dec 6, 2021

Lakeside Inn
The Constitution Inn

The Constitution Inn

3.5 out of 5
150 3rd Ave, Boston, MA, 02129
Stay at this 3.5-star business-friendly hotel in Boston. Enjoy free WiFi, free parking, and an indoor pool. Our guests praise the helpful staff in our reviews. ...
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, 2116
The price is $236 per night from Jun 6 to Jun 7
Stay at this business-friendly hostel in Boston. Enjoy free WiFi, a 24-hour front desk, and a library. Our guests praise the breakfast and the helpful staff ...
4.7/5 Exceptional! (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.

Fly From Chicago to Boston

Origin Chicago
Destination Boston
Number of Daily Flights 65
Earliest Flight Departure Date May 28
Latest Flight Departure Date May 29
Popular Airlines American Airlines

On a budget? Book a flight with CheapTickets to get affordable Chicago to Boston flights with a couple of well-aimed clicks.

Flights from Chicago to Boston depart from the Chicago O'Hare International Airport (ORD), the second-largest airport in the United States. One can get from the Chicago Loop to the airport in only thirty minutes, paying an affordable taxi fare of about $30. However, in heavy traffic it is best to take the Chicago Transit Authority (CTA) bus to ORD to bypass such traffic, and you can get an unlimited pass for the day for just under $6, or pay a single ride fare for $2.25. Needless to say, taking the bus is definitely cost efficient.

After arriving safely to ORD and boarding your plane, you can relax and rest easy for just two hours and thirty minutes as you traverse over 800 miles to Boston, Massachusetts. You will arrive at the Logan International Airport (BOS), also known as the General Edward Lawrence International Airport. Boston experiences all the seasons, with winter and summer getting extreme. In the winter months, it's best to pack some winter clothes and boots because it is located so far towards the north. Of course, if you're coming from Chicago, you might already be prepared. After your arrival, you can catch a taxi or bus to your hotel immediately. Or, if you are more interested in checking out the city, you can travel by taxi to anywhere within the 5 mile radius affordably using the MBTA subways.

*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.