Cheap flights from Massachusetts to Chicago
Travel > North America > United States > Massachusetts to Chicago flights
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.... (read more in our Chicago Travel Guide)
Check current prices for flights to Chicago at our partners' sites:
Search and Compare cheap Flights
Cheapest flights found for the next 6 months
(click city name to see more / use right arrow to view later months)| From |
| more | |||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Boston | |||||||||||||||||||||||||||||||
Check our newest flight offers to Chicago:
- $120
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 04/09/2025 06:09 pm Chicago, IL (ORD) Boston, MA (BOS) 04/15/2025 01:47 pm - $125
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Boston, MA (BOS) Chicago, IL (ORD) 04/09/2025 06:09 pm Chicago, IL (ORD) Boston, MA (BOS) 04/15/2025 09:32 am
Recently found cheap flight deals
Las Vegas To Panama City Multiple Airlines airfares from Las Vegas in August
$1108 Depart: 08/20/2024
Return: 09/03/2024
provided by Cheapoair.com
Kansas City To Cebu Major Carrier airfares from Kansas City in March
$2183 Depart: 03/19/2025
Return: 03/29/2025
provided by Cheapoair.com
Birmingham To Saint Croix American Airlines airfares from Birmingham in November
$860 Depart: 11/03/2019
Return: 11/11/2019
provided by Cheapoair.com
Houston To Great Falls Alaska Airlines airfares from Houston in July
$651 Depart: 07/31/2024
Return: 08/06/2024
provided by Cheapoair.com
Chicago To Veracruz Multiple Airlines airfares from Chicago in April
$343 Depart: 04/09/2025
Return: 04/14/2025
provided by Cheapoair.com
Bloomington To Tucson American Airlines airfares from Bloomington in March
$806 Depart: 03/27/2017
Return: 04/02/2017
provided by Flightnetwork
Salt Lake City To Mcallen Alaska Airlines airfares from Salt Lake City in June
$3136 Depart: 06/14/2022
Return: 07/05/2022
provided by Cheapoair.com
Providence To Myrtle Beach Mexicana Airlines airfares from Providence in March
$230 Depart: 03/17/2025
Return: 03/30/2025
provided by Cheapoair.com
Houston To Biloxi/Gulfport United Airlines airfares from Houston in July
$297 Depart: 07/23/2019
Return: 08/03/2019
provided by FlyFar
Specify your search details. Browse the cheapest flights from Massachusetts to Chicago, Chicago hotel rooms and Massachusetts to Chicago vacation packages from the most popular providers, airline consolidators and travel search engines.
© Copyright 2004 - 2025 Travelgrove, Inc.