Cheap flights from Boston to Chicago
Travel > North America > United States > Boston to Chicago flights
Travel tip: Visit Chicago on your holidays!Check our current prices for flights from Boston to Chicago. 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 Boston to Chicago, you will need to run a search below.
Search and Compare cheap Flights

Book your flight now with and save!
Cheap airfares from /OW are provided by . This flight is going on , from () airport and arrives to () at so it makes 0 hours and 0 minutes. This is a oneway flight. Date posted: 31 Dec 1969
Price evolution for flights From Boston To Chicago

Recent Deals on Flights from Boston to Chicago:Roundtrip / Oneway
- Unfortunately no offers could be found for this route.
Please search directly on the main page using the searchbox to find the best flights.
Recently found cheap flight deals
Phoenix To Venice Multiple Airlines airfares from Phoenix in January
$896 Depart: 01/06/2025
Return: 01/16/2025
provided by Cheapoair.com
Las Vegas To Johannesburg Qatar Airways airfares from Las Vegas in March
$1492 Depart: 03/20/2025
Return: 04/03/2025
provided by Cheapoair.com
Montreal To San Jose Multiple Airlines airfares from Montreal in May
$652 Depart: 05/27/2025
Return: 06/04/2025
provided by Cheapoair.com
Fort Lauderdale To San Juan Multiple Airlines airfares from Fort Lauderdale in April
$140 Depart: 04/10/2025
Return: 04/25/2025
provided by Cheapoair.com
Toronto To Oslo Multiple Airlines airfares from Toronto in March
$975 Depart: 03/23/2025
Return: 03/28/2025
provided by Cheapoair.com
Moline To Atlanta Alaska Airlines airfares from Moline in December
$2698 Depart: 12/31/2019
Return: 01/08/2020
provided by Cheapoair.com
Winnipeg To Las Vegas Multiple Airlines airfares from Winnipeg in April
$334 Depart: 04/04/2025
Return: 04/16/2025
provided by Cheapoair.com
Phoenix To Calcutta Multiple Airlines airfares from Phoenix in March
$1475 Depart: 03/19/2025
Return: 03/27/2025
provided by Cheapoair.com
Sarasota To Charlotte Multiple Airlines airfares from Sarasota in May
$5547 Depart: 05/21/2021
Return: 06/03/2021
provided by Cheapoair.com
Specify your search details. Browse the cheapest flights from Boston to Chicago, Chicago hotel rooms and Boston to Chicago vacation packages from the most popular providers, airline consolidators and travel search engines.
Know what to do when flying to Chicago?
Chicago Travel Guide Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals. Though [...]Chicago History The site where Chicago stands had long been considered as an important portage point on the water route linking the Great Lakes with the Mississippi river. Aside from this important fact, there are a lot of interesting things you need to know [...]
Chicago Sightseeing The rich cultural heritage of Chicago is depicted in its famous sights. Other tourist attractions in the city can be seen in zoos and parks as well. If you are thinking about visiting, it will help if you take a look at some of the travel [...]
Chicago Nightlife Chicago is one of the cities blessed with a variety of nightlife options. Discos, clubs, bars - name it and the place will certainly give you the pleasure you are looking for. You will surely dance the night away as you listen to the music [...]