Cheap flights from Chicago to Boston
Travel > North America > United States > Chicago to Boston flights
Travel tip: Visit Boston on your holidays!Check our current prices for flights from Chicago to Boston. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Boston, you will need to run a search below.
Search and Compare cheap Flights

Book your flight now with Cheapoair.com and save!
Cheap Boston airfares from $255/RT are provided by Cheapoair.com. Outbound flight is leaving on 08/24/2022, 10:18 am from Chicago O`hare (ORD) airport and arrives at Boston Logan (BOS) at 04:52 pm. The flight time is 6 hours and 34 minutes. The Returning flight departes on 09/06/2022, 07:10 am (other return dates are also available). Date posted: 26 Mar 2022
Price evolution for flights From Chicago To Boston

Recent Deals on Flights from Chicago to Boston:Roundtrip / Oneway
- $255
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 08/24/2022 10:18 am Boston, MA (BOS) Chicago, IL (ORD) 09/06/2022 07:10 am - $273
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 08/02/2022 06:00 pm Boston, MA (BOS) Chicago, IL (ORD) 08/17/2022 07:10 am - $448
Sun Country Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/20/2022 07:00 pm Boston, MA (BOS) Chicago, IL (ORD) 07/04/2022 11:30 am - $461
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/20/2022 06:45 pm Boston, MA (BOS) Chicago, IL (ORD) 07/04/2022 11:13 am - $652
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 08/02/2022 06:00 pm Boston, MA (BOS) Chicago, IL (ORD) 08/17/2022 05:25 pm - $100
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/07/2022 06:20 pm - $148
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/09/2022 04:45 pm - $172
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/13/2022 11:05 am - $227
Sun Country Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/09/2022 06:55 pm - $525
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Boston, MA (BOS) 06/13/2022 08:02 pm
Recently found cheap flight deals
Dallas To Chennai Gulf Air Bahrain airfares from Dallas in June
$2194 Depart: 06/04/2022
Return: 06/15/2022
provided by Cheapoair.com
Houston To Berlin Multiple Airlines airfares from Houston in July
$1408 Depart: 07/08/2021
Return: 07/20/2021
provided by Cheapoair.com
Spartanburg To San Jose Multiple Airlines airfares from Spartanburg in June
$1706 Depart: 06/07/2022
Return: 06/18/2022
provided by Cheapoair.com
Omaha To Tucson Alaska Airlines airfares from Omaha in August
$1117 Depart: 08/02/2022
Return: 08/16/2022
provided by Cheapoair.com
Seattle To Saint Louis Multiple Airlines airfares from Seattle in September
$311 Depart: 09/14/2021
Return: 09/29/2021
provided by Cheapoair.com
Dallas To Kozhikode Qatar Airways airfares from Dallas in September
$1769 Depart: 09/22/2021
Return: 09/29/2021
provided by Cheapoair.com
Newport News To Atlanta Oceanic Airlines airfares from Newport News in August
$10332 Depart: 08/04/2020
Return: 08/12/2020
provided by FlyFar
Tampa To Munich Multiple Airlines airfares from Tampa in June
$1232 Depart: 06/01/2022
Return: 06/07/2022
provided by Cheapoair.com
Colorado Springs To Kona Multiple Airlines airfares from Colorado Springs in April
$860 Depart: 04/11/2020
Return: 04/19/2020
provided by Cheapoair.com
Specify your search details. Browse the cheapest flights from Chicago to Boston, Boston hotel rooms and Chicago to Boston vacation packages from the most popular providers, airline consolidators and travel search engines.
Know what to do when flying to Boston?
Boston Travel Guide Boston is US nation's history and myth capital. It was, until 1755, the biggest city in America and the most directly affected by the British Crown (you can see that if you only consider that it has the same name as the city in UK). [...]Boston History On the 17th of September 1630, Boston was established by English Puritan colonists. The Puritans are confused sometimes with Pilgrims, who established Plymouth 10 years before in what we know as Barnstable County, Plymouth County, and [...]
Boston Sightseeing There are many things that you can see and do in Boston because of its historic and cultural background. One of the many museums that you can visit is the Boston Museum of Fine Arts, which is a smaller version of the Metropolitan Museum of [...]
Boston Nightlife There are many places that you can go to for enjoying nightlife in Boston, Massachusetts. One of these is called Kings, offering a variety of activities and a diverse clientèle. During the night, Kings brings a lengthy wait for tables [...]