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Cheap flights from Massachusetts to Chicago O'Hare Intl Airport from $45

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 O'Hare Intl Airport departing on 12/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Massachusetts to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Massachusetts to Chicago.

Cheap last minute flights

Planning a quick getaway from Massachusetts to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Massachusetts to Chicago

Find recent round-trip train or bus tickets from Massachusetts to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
5:38 pm - 12:35 amORD-BOS
5h 57m1 stop
Tue, Dec 10 - Tue, Dec 17
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
Mon, Dec 9 - Tue, Dec 10
6:00 am - 11:47 amBOS-ORD
6h 47m1 stop
4:53 pm - 12:30 amORD-BOS
6h 37m1 stop
$106Frontier
Find Deal
Wed, Jan 8 - Mon, Jan 13
6:00 am - 1:34 pmBOS-ORD
8h 34m1 stop
12:42 pm - 12:30 amORD-BOS
10h 48m1 stop
$108Frontier
Find Deal
Tue, Jan 14 - Wed, Jan 15
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$126Spirit Airlines
Find Deal
Tue, Dec 3 - Tue, Dec 10
10:34 am - 9:07 pmBOS-ORD
11h 33m1 stop
8:20 am - 11:42 pmORD-BOS
14h 22m1 stop
$129Spirit Airlines
Find Deal
Tue, Dec 10 - Sat, Dec 14
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$157United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
10:14 am - 3:43 pmORD-BOS
4h 29m1 stop
$161JetBlue
Find Deal
Wed, Dec 11 - Wed, Dec 11
11:25 am - 3:28 pmBOS-ORD
5h 03m1 stop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$166JetBlue
Find Deal
Fri, Jan 10 - Mon, Jan 13
7:38 pm - 11:20 pmBOS-ORD
4h 42m1 stop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$167United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$45Spirit Airlines
Find Deal
Tue, Dec 10
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$46Spirit Airlines
Find Deal
Tue, Dec 10
6:00 am - 11:47 amBOS-ORD
6h 47m1 stop
$54Frontier
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Wed, Jan 8
6:00 am - 12:45 pmBOS-ORD
7h 45m1 stop
$57Frontier
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Wed, Feb 5
7:45 pm - 9:43 pmBOS-ORD
2h 58mnonstop
$79Delta
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Sat, Dec 14
11:25 am - 3:28 pmBOS-ORD
5h 03m1 stop
$88JetBlue
Find Deal
Thu, Jan 9
3:50 pm - 5:53 pmBOS-ORD
3h 03mnonstop
$89JetBlue
Find Deal
Tue, Jan 7
5:50 pm - 4:06 pmBDL-ORD
23h 16m2 stops
Mon, Dec 9
3:45 pm - 5:46 pmBOS-ORD
3h 01mnonstop
$95Delta
Find Deal
Thu, Nov 21
5:50 pm - 4:06 pmBDL-ORD
23h 16m2 stops
Mon, Dec 16
10:55 am - 9:45 pmBOS-ORD
11h 50m1 stop
2:15 pm - 12:29 amORD-BOS
9h 14m1 stop
$124Frontier
Find Deal
Sat, Nov 16 - Wed, Nov 20
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$130Spirit Airlines
Find Deal
Tue, Nov 19 - Sun, Nov 24
11:24 am - 12:38 amBOS-ORD
14h 14m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Mon, Nov 18 - Sat, Nov 23
11:24 am - 12:38 amBOS-ORD
14h 14m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Mon, Nov 18 - Thu, Nov 21
2:30 pm - 4:26 pmBOS-ORD
2h 56mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$268Delta
Find Deal
Sat, Nov 16 - Thu, Nov 21
11:15 am - 4:52 pmBOS-ORD
6h 37m1 stop
7:15 am - 10:40 amORD-BOS
2h 25mnonstop
$278Delta
Find Deal
Tue, Nov 19 - Sat, Nov 23
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
9:25 am - 12:50 pmORD-BOS
2h 25mnonstop
$297United Airlines
Find Deal
Sat, Nov 16 - Wed, Nov 20
5:01 am - 9:03 amBOS-ORD
5h 02m1 stop
6:00 am - 9:17 amORD-BOS
2h 17mnonstop
$306JetBlue
Find Deal
Tue, Nov 19 - Sun, Nov 24
2:14 pm - 4:08 pmBOS-ORD
2h 54mnonstop
12:15 pm - 3:28 pmORD-BOS
2h 13mnonstop
$312JetBlue
Find Deal
Tue, Nov 19 - Thu, Nov 21
7:55 pm - 7:48 amBDL-ORD
12h 53m2 stops
10:55 am - 2:07 pmORD-BDL
2h 12mnonstop
$318United Airlines
Find Deal
Fri, Nov 15 - Sat, Nov 16
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$139Spirit Airlines
Find Deal
Mon, Nov 25 - Thu, Nov 28
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$148Spirit Airlines
Find Deal
Sun, Nov 24 - Thu, Nov 28
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
10:30 am - 1:52 pmORD-BOS
2h 22mnonstop
$155Delta
Find Deal
Mon, Dec 9 - Wed, Dec 11
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$156JetBlue
Find Deal
Mon, Dec 9 - Mon, Dec 16
7:50 pm - 9:51 pmBOS-ORD
3h 01mnonstop
2:05 pm - 5:34 pmORD-BOS
2h 29mnonstop
$157Delta
Find Deal
Wed, Dec 4 - Fri, Dec 13
5:10 am - 7:16 amBOS-ORD
3h 06mnonstop
8:12 am - 11:27 amORD-BOS
2h 15mnonstop
$160American Airlines
Find Deal
Sat, Dec 7 - Mon, Dec 9
2:41 pm - 4:41 pmBOS-ORD
3h 00mnonstop
7:00 am - 10:28 amORD-BOS
2h 28mnonstop
$162American Airlines
Find Deal
Wed, Dec 4 - Sun, Dec 8
3:50 pm - 5:53 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$167JetBlue
Find Deal
Wed, Jan 8 - Mon, Jan 13
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
3:50 pm - 7:11 pmORD-BOS
2h 21mnonstop
$173United Airlines
Find Deal
Mon, Nov 25 - Wed, Dec 4
9:30 am - 11:28 amBOS-ORD
2h 58mnonstop
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
$181United Airlines
Find Deal
Fri, Jan 17 - Mon, Jan 20

United Airlines flights from Massachusetts to Chicago O'Hare Intl Airport

Our best United Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
United Airlines
Dec 6
BOS6:28 pmBoston Logan Intl
2h 56m
ORD8:24 pmChicago O'Hare Intl
Dec 8
ORD9:20 amChicago O'Hare Intl
2h 25m
BOS12:45 pmBoston Logan Intl
United Airlines
Dec 6
BOS7:38 pmBoston Logan Intl
4h 42m
1 stop
ORD11:20 pmChicago O'Hare Intl
Dec 8
ORD9:20 amChicago O'Hare Intl
2h 25m
BOS12:45 pmBoston Logan Intl
United Airlines
Dec 12
BOS6:00 amBoston Logan Intl
5h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Dec 19
ORD1:55 pmChicago O'Hare Intl
2h 23m
BOS5:18 pmBoston Logan Intl

Frontier flights from Massachusetts to Chicago O'Hare Intl Airport

Our best Frontier deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
Frontier
Jan 8
BOS6:00 amBoston Logan Intl
6h 47m
1 stop
ORD11:47 amChicago O'Hare Intl
Jan 13
ORD4:53 pmChicago O'Hare Intl
6h 37m
1 stop
BOS12:30 amBoston Logan Intl
Frontier
Jan 14
BOS6:00 amBoston Logan Intl
8h 34m
1 stop
ORD1:34 pmChicago O'Hare Intl
Jan 15
ORD12:42 pmChicago O'Hare Intl
10h 48m
1 stop
BOS12:30 amBoston Logan Intl
Frontier
Dec 16
BOS8:54 amBoston Logan Intl
7h 49m
1 stop
ORD3:43 pmChicago O'Hare Intl
Dec 17
ORD5:38 pmChicago O'Hare Intl
5h 57m
1 stop
BOS12:35 amBoston Logan Intl

How to get the cheapest flight ticket from Massachusetts to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport from Massachusetts?

Spirit Airlines. Spirit Airlines, Frontier, and JetBlue are the most popular carriers operating from Massachusetts to Chicago O'Hare Intl Airport

What cabin class options are available on Massachusetts to Chicago O'Hare Intl Airport flights?

There are 4 cabin classes available to choose from on Massachusetts to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

You could potentially save up to 13% on your flight if you consider stops on a Massachusetts to Chicago O'Hare Intl Airport flight.

Cheap Massachusetts to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago O'Hare Intl Airport

Best Price Found

$45

Fastest flight time

2h 33m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Massachusetts in the past 72 hours is $45. The best round-trip flight deal from Massachusetts to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $103.
The fastest flight from Massachusetts to Chicago O'Hare Intl Airport takes 2h 33m
Direct flights go from Massachusetts to Chicago O'Hare Intl Airport every day.

  • When did momondo last update prices for flights from Massachusetts to Chicago O'Hare Intl Airport?

    Prices for flights from Massachusetts to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Massachusetts to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Massachusetts to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Massachusetts to Chicago O'Hare Intl Airport?


Best airlines flying from Massachusetts to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Massachusetts to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $39Free CancellationRating
6.3
8,167 reviews
Search Spirit Airlines flights
JetBluePriceFrom $84Free CancellationRating
7.5
3,447 reviews
Search JetBlue flights
DeltaPriceFrom $93Free CancellationRating
8.0
8,788 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
American AirlinesPriceFrom $134Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $149Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Massachusetts to Chicago for you.

Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?

All flight searches from Massachusetts to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Massachusetts and alert you when they change.


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