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Lowest round trip fares by airline from Chicago and Boston

Cheapest prices ($32 One Way, $75 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
The price is $89 per night from May 19 to May 20
$89
per night
May 19 - May 20
Book a stay at this business-friendly hotel in Wakefield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
7/10 Good! (1,567 reviews)
Return guest
"We stayed here before and loved it. We came back for a two-night stay. Lisa and Abraham are so warm and welcoming. They go above and beyond to make the guests comfortable. The room has every you need plus a great view."

Reviewed on May 9, 2024

Lakeside Inn
The Constitution Inn

The Constitution Inn

3.5 out of 5
150 3rd Ave, Boston, MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions TD Garden and Boston Harbor ...
6.6/10 (1,000 reviews)
Comfortable but bad parking situation
"Only downside was the parking garage which cost $16/day and the ice machine was broken. Bed was very comfortable and staff was kind. Room was also clean and elevator was fast."

Reviewed on Oct 25, 2020

The Constitution Inn
HI Boston - Hostel

HI Boston - Hostel

2 out of 5
19 Stuart Street, Boston, MA
The price is $159 per night from May 12 to May 13
$159
per night
May 12 - May 13
Stay at this hostel in Boston. Enjoy free WiFi, a 24-hour front desk, and a fireplace in the lobby. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,003 reviews)
"Amazing staff, they speak clearly and communicate well. Fun time getting to know others. Close to real good food and shops. Would visit again"

Reviewed on May 6, 2024

HI Boston - Hostel
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
59
Earliest Flight Departure Date
May 18
Latest Flight Departure Date
May 19
Popular Airlines
JetBlue

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.