Cheap flights from Massachusetts to Chicago from $42
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Chicago departing on 9/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Round-trip
1 adult
Economy
0 bags
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Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Massachusetts to Chicago by changing tabs
Spirit Airlines![Spirit Airlines]()
Oct 17![Spirit Airlines]()
Oct 19
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
Alaska Airlines![Alaska Airlines]()
Sep 28![Alaska Airlines]()
Sep 30
BOS7:14 amBoston Logan Intl
17h 34m
2 stops
ORD11:48 pmChicago O'Hare Intl
ORD7:00 amChicago O'Hare Intl
15h 59m
2 stops
BOS11:59 pmBoston Logan Intl
Multiple Airlines![Multiple Airlines]()
Sep 3![Multiple Airlines]()
Sep 10
BOS6:00 amBoston Logan Intl
6h 59m
1 stop
ORD11:59 amChicago O'Hare Intl
ORD4:30 pmChicago O'Hare Intl
5h 22m
1 stop
BOS10:52 pmBoston Logan Intl
Spirit Airlines![Spirit Airlines]()
Sep 10![Spirit Airlines]()
Sep 14
BOS2:30 pmBoston Logan Intl
9h 07m
1 stop
ORD10:37 pmChicago O'Hare Intl
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
Frontier![Frontier]()
Sep 11![Frontier]()
Sep 14
BOS6:00 amBoston Logan Intl
4h 50m
1 stop
MDW9:50 amChicago Midway
MDW3:00 pmChicago Midway
8h 29m
1 stop
BOS12:29 amBoston Logan Intl
Find the cheapest one-way flights from Massachusetts to Chicago
If you're looking for one-way flights from Massachusetts to Chicago, view some of our deals below provided by Frontier, Southwest and Spirit Airlines
Find the cheapest direct flights from Massachusetts to Chicago
Spirit Airlines![Spirit Airlines]()
Aug 27![Spirit Airlines]()
Aug 31
BOS8:00 amBoston Logan Intl
2h 53m
ORD9:53 amChicago O'Hare Intl
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
Delta![Delta]()
Sep 5![Delta]()
Sep 6
BOS7:30 amBoston Logan Intl
3h 00m
ORD9:30 amChicago O'Hare Intl
ORD6:35 amChicago O'Hare Intl
2h 26m
BOS10:01 amBoston Logan Intl
Southwest![Southwest]()
Oct 5![Southwest]()
Oct 7
BOS6:10 amBoston Logan Intl
2h 45m
MDW7:55 amChicago Midway
MDW2:05 pmChicago Midway
2h 15m
BOS5:20 pmBoston Logan Intl
United Airlines![United Airlines]()
Nov 1![United Airlines]()
Nov 3
ALB6:00 amAlbany Intl
2h 33m
ORD7:33 amChicago O'Hare Intl
ORD7:40 amChicago O'Hare Intl
2h 08m
ALB10:48 amAlbany Intl
JetBlue![JetBlue]()
Aug 27![JetBlue]()
Sep 4
BOS6:30 amBoston Logan Intl
2h 50m
ORD8:20 amChicago O'Hare Intl
ORD10:50 amChicago O'Hare Intl
2h 25m
BOS2:15 pmBoston Logan Intl
Search last-minute flights to Chicago from Massachusetts
Find and compare round-trip flight prices for your last-minute flight from Massachusetts to Chicago
Spirit Airlines![Spirit Airlines]()
Aug 29![Spirit Airlines]()
Sep 5
BOS5:48 amBoston Logan Intl
2h 52m
ORD7:40 amChicago O'Hare Intl
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
Frontier![Frontier]()
Aug 27![Frontier]()
Aug 28
BOS6:00 amBoston Logan Intl
8h 35m
1 stop
MDW1:35 pmChicago Midway
MDW11:05 amChicago Midway
12h 26m
1 stop
BOS12:31 amBoston Logan Intl
Multiple Airlines![Multiple Airlines]()
Aug 27![Multiple Airlines]()
Aug 27
BOS6:00 amBoston Logan Intl
6h 59m
1 stop
ORD11:59 amChicago O'Hare Intl
ORD8:59 pmChicago O'Hare Intl
2h 28m
BOS12:27 amBoston Logan Intl
American Airlines![American Airlines]()
Aug 30![American Airlines]()
Sep 4
BOS5:15 amBoston Logan Intl
2h 55m
ORD7:10 amChicago O'Hare Intl
ORD1:15 pmChicago O'Hare Intl
2h 22m
BOS4:37 pmBoston Logan Intl
Southwest![Southwest]()
Aug 30![Southwest]()
Sep 5
BOS6:50 amBoston Logan Intl
2h 35m
MDW8:25 amChicago Midway
MDW8:40 amChicago Midway
2h 25m
BOS12:05 pmBoston Logan Intl
Spirit Airlines flights from Massachusetts to Chicago
Our best Spirit Airlines deals on Massachusetts to Chicago flight tickets
Spirit Airlines![Spirit Airlines]()
Oct 17![Spirit Airlines]()
Oct 19
BOS11:35 amBoston Logan Intl
2h 52m
ORD1:27 pmChicago O'Hare Intl
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
Spirit Airlines![Spirit Airlines]()
Sep 10![Spirit Airlines]()
Sep 14
BOS2:30 pmBoston Logan Intl
9h 07m
1 stop
ORD10:37 pmChicago O'Hare Intl
ORD2:17 pmChicago O'Hare Intl
2h 25m
BOS5:42 pmBoston Logan Intl
United Airlines flights from Massachusetts to Chicago
Our best United Airlines deals on Massachusetts to Chicago flight tickets
United Airlines![United Airlines]()
Sep 18![United Airlines]()
Sep 19
BOS6:00 amBoston Logan Intl
2h 48m
ORD7:48 amChicago O'Hare Intl
ORD6:00 amChicago O'Hare Intl
2h 26m
BOS9:26 amBoston Logan Intl
United Airlines![United Airlines]()
Nov 1![United Airlines]()
Nov 3
ALB6:00 amAlbany Intl
2h 33m
ORD7:33 amChicago O'Hare Intl
ORD7:40 amChicago O'Hare Intl
2h 08m
ALB10:48 amAlbany Intl
How to get the cheapest flight ticket from Massachusetts to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest airline that flies to Chicago from Massachusetts?
Alaska Airlines. Alaska Airlines, Spirit Airlines, and Frontier are the most popular carriers operating from Massachusetts to Chicago
What is the cheapest Massachusetts to Chicago flight route?
Boston Logan Intl - Chicago O'Hare Intl. Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Massachusetts - Chicago flight prices
What cabin class options are available on Massachusetts to Chicago flights?
There are 4 cabin classes available to choose from on Massachusetts to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Massachusetts to Chicago flights?
No. A direct flight is the cheapest option for a flight between Massachusetts to Chicago.
Cheap Massachusetts to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago
When did momondo last update prices for flights from Massachusetts to Chicago?
Prices for flights from Massachusetts to Chicago are updated daily.
How many operators does momondo search for flights from Massachusetts to Chicago?
There are 8 operators available for flights from Massachusetts to Chicago as of August 2024.
How old do you have to be to fly from Massachusetts to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
Best airlines flying from Massachusetts to Chicago
Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $39 | Free Cancellation | Rating 8.0 9,382 reviews | |||
| PriceFrom $42 | Free Cancellation | Rating 6.3 8,324 reviews | |||
| PriceFrom $85 | Free Cancellation | Rating 7.6 3,821 reviews | |||
| PriceFrom $90 | Free Cancellation | Rating 6.2 3,783 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 8.0 9,363 reviews | |||
| PriceFrom $137 | Free Cancellation | Rating 7.3 10,000 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 8.1 5,457 reviews | |||
| PriceFrom $147 | Free Cancellation | Rating 7.4 9,798 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Massachusetts to Chicago?
It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Massachusetts which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Massachusetts to Chicago?
Once all potential Massachusetts to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Massachusetts to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.
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