Cheap flights from Chicago to Massachusetts from $66
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Massachusetts departing on 5/11. 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
From?
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Fri 5/3
Fri 5/10
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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 Chicago to Massachusetts by changing tabs
Frontier![Frontier]()
May 11![Frontier]()
May 13
MDW8:17 pmChicago Midway
10h 51m
1 stop
BOS8:08 amBoston Logan Intl
BOS12:41 pmBoston Logan Intl
11h 49m
1 stop
MDW11:30 pmChicago Midway
Multiple Airlines![Multiple Airlines]()
May 31![Multiple Airlines]()
Jun 2
ORD8:30 pmChicago O'Hare Intl
13h 03m
1 stop
BOS10:33 amBoston Logan Intl
BOS1:53 pmBoston Logan Intl
6h 52m
1 stop
ORD7:45 pmChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
May 6![Spirit Airlines]()
May 11
ORD10:00 pmChicago O'Hare Intl
21h 45m
2 stops
BOS8:45 pmBoston Logan Intl
BOS10:27 pmBoston Logan Intl
14h 07m
1 stop
ORD11:34 amChicago O'Hare Intl
JetBlue![JetBlue]()
Jun 1![JetBlue]()
Jun 4
ORD7:15 pmChicago O'Hare Intl
2h 26m
BOS10:41 pmBoston Logan Intl
BOS4:25 pmBoston Logan Intl
2h 55m
ORD6:20 pmChicago O'Hare Intl
American Airlines![American Airlines]()
Jun 8![American Airlines]()
Jun 9
ORD8:36 pmChicago O'Hare Intl
2h 25m
BOS12:01 amBoston Logan Intl
BOS5:18 amBoston Logan Intl
2h 55m
ORD7:13 amChicago O'Hare Intl
Find the cheapest one-way flights from Chicago to Massachusetts
If you're looking for one-way flights from Chicago to Massachusetts, view some of our deals below provided by American Airlines, Frontier and JetBlue
Search last-minute flights to Massachusetts from Chicago
Find and compare round-trip flight prices for your last-minute flight from Chicago to Massachusetts
Frontier![Frontier]()
May 4![Frontier]()
May 11
MDW8:17 pmChicago Midway
10h 51m
1 stop
BOS8:08 amBoston Logan Intl
BOS12:41 pmBoston Logan Intl
11h 00m
1 stop
MDW10:41 pmChicago Midway
Spirit Airlines![Spirit Airlines]()
May 6![Spirit Airlines]()
May 11
ORD10:00 pmChicago O'Hare Intl
21h 45m
2 stops
BOS8:45 pmBoston Logan Intl
BOS10:27 pmBoston Logan Intl
14h 07m
1 stop
ORD11:34 amChicago O'Hare Intl
Multiple Airlines![Multiple Airlines]()
May 4![Multiple Airlines]()
May 6
ORD8:25 amChicago O'Hare Intl
22h 43m
1 stop
BOS8:08 amBoston Logan Intl
BOS7:43 pmBoston Logan Intl
13h 54m
1 stop
ORD8:37 amChicago O'Hare Intl
JetBlue![JetBlue]()
May 8![JetBlue]()
May 13
ORD8:40 amChicago O'Hare Intl
2h 29m
BOS12:09 pmBoston Logan Intl
BOS6:10 amBoston Logan Intl
2h 54m
ORD8:04 amChicago O'Hare Intl
American Airlines![American Airlines]()
May 6![American Airlines]()
May 8
ORD8:29 pmChicago O'Hare Intl
2h 26m
BOS11:55 pmBoston Logan Intl
BOS5:25 amBoston Logan Intl
2h 56m
ORD7:21 amChicago O'Hare Intl
Best airlines flying from Chicago to Massachusetts
Compare and see reviews for airlines that fly from Chicago to Massachusetts with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $69 | Free Cancellation | Rating 8.1 9,110 reviews | |||
| PriceFrom $69 | Free Cancellation | Rating 7.6 4,582 reviews | |||
| PriceFrom $84 | Free Cancellation | Rating 7.4 11,221 reviews | |||
| PriceFrom $89 | Free Cancellation | Rating 8.0 10,932 reviews | |||
| PriceFrom $104 | Free Cancellation | Rating 6.4 8,739 reviews | |||
| PriceFrom $114 | Free Cancellation | Rating 7.3 14,844 reviews |
Frontier flights from Chicago to Massachusetts
Our best Frontier deals on Chicago to Massachusetts flight tickets
Frontier![Frontier]()
May 11![Frontier]()
May 13
MDW8:17 pmChicago Midway
10h 51m
1 stop
BOS8:08 amBoston Logan Intl
BOS12:41 pmBoston Logan Intl
11h 49m
1 stop
MDW11:30 pmChicago Midway
Frontier![Frontier]()
May 4![Frontier]()
May 11
MDW8:17 pmChicago Midway
10h 51m
1 stop
BOS8:08 amBoston Logan Intl
BOS12:41 pmBoston Logan Intl
11h 00m
1 stop
MDW10:41 pmChicago Midway
JetBlue flights from Chicago to Massachusetts
Our best JetBlue deals on Chicago to Massachusetts flight tickets
JetBlue![JetBlue]()
Jun 1![JetBlue]()
Jun 4
ORD7:15 pmChicago O'Hare Intl
2h 26m
BOS10:41 pmBoston Logan Intl
BOS4:25 pmBoston Logan Intl
2h 55m
ORD6:20 pmChicago O'Hare Intl
JetBlue![JetBlue]()
May 25![JetBlue]()
May 29
ORD7:15 pmChicago O'Hare Intl
2h 26m
BOS10:41 pmBoston Logan Intl
BOS6:10 amBoston Logan Intl
2h 54m
ORD8:04 amChicago O'Hare Intl
How to get the cheapest flight ticket from Chicago to Massachusetts
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 Massachusetts from Chicago?
Alaska Airlines. Alaska Airlines, Delta, and JetBlue are the most popular carriers operating from Chicago to Massachusetts
What is the cheapest Chicago to Massachusetts flight route?
Chicago O'Hare Intl - Boston Logan Intl. Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Massachusetts flight prices
What cabin class options are available on Chicago to Massachusetts flights?
There are 4 cabin classes available to choose from on Chicago to Massachusetts 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 Chicago to Massachusetts flights?
You could potentially save up to 1% on your flight if you consider stops on a Chicago to Massachusetts flight.
Cheap Chicago to Massachusetts flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Massachusetts
Best Price Found | $66 |
|---|---|
Fastest flight time | 2h 17m |
Direct flights | Every day |
Airports in Massachusetts | 3 airports |
When did momondo last update prices for flights from Chicago to Massachusetts?
Prices for flights from Chicago to Massachusetts were last updated today.
How many operators does momondo search for flights from Chicago to Massachusetts?
The number of operators available for flights from Chicago to Massachusetts is 7 as of April 2024.
How old do you have to be to fly from Chicago to Massachusetts?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Massachusetts.
What documentation or ID do you need to fly to Massachusetts?
The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Massachusetts?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Massachusetts from Chicago.
Can I find flights from Chicago to Massachusetts with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Massachusetts from Chicago with this policy.
How can momondo help me find flights from Chicago to Massachusetts?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Massachusetts.
I’m not ready to book a flight from Chicago to Massachusetts right now. Can momondo alert me if prices change?
Price alerts on flights to Massachusetts from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.
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