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Cheap flights from Boston to Chicago from $46

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 2/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Boston to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Boston 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 Boston to Chicago.

Cheap last minute flights

Planning a quick getaway from Boston 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 Boston to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:00 am - 1:36 pmBOS-ORD
8h 36m1 stop
2:59 pm - 12:39 amORD-BOS
8h 40m1 stop
$102Frontier
Find Deal
Tue, Feb 4 - Tue, Feb 11
6:00 am - 4:14 pmBOS-MDW
11h 14m1 stop
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$106Frontier
Find Deal
Tue, Jan 14 - Tue, Jan 21
7:00 am - 9:00 amBOS-ORD
3h 00mnonstop
9:05 am - 12:23 pmORD-BOS
2h 18mnonstop
$157JetBlue
Find Deal
Sat, Jan 18 - Thu, Jan 23
8:45 am - 10:50 amBOS-ORD
3h 05mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$159American Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 19
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
6:45 pm - 10:12 pmORD-BOS
2h 27mnonstop
$160American Airlines
Find Deal
Mon, Jan 20 - Mon, Jan 27
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
9:05 am - 12:23 pmORD-BOS
2h 18mnonstop
$166JetBlue
Find Deal
Sun, Jan 19 - Thu, Jan 23
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
9:20 am - 12:46 pmORD-BOS
2h 26mnonstop
$212United Airlines
Find Deal
Fri, Jan 3 - Wed, Jan 8
7:00 am - 9:01 amBOS-ORD
3h 01mnonstop
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$223Delta
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Wed, Apr 16 - Thu, Apr 24
5:20 am - 1:28 pmBOS-ORD
9h 08m1 stop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$237Delta
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Sat, Jan 18 - Sun, Jan 19
10:25 am - 2:48 pmBOS-ORD
5h 23m1 stop
6:00 am - 2:07 pmORD-BOS
7h 07m1 stop
$246United Airlines
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:00 am - 1:36 pmBOS-ORD
8h 36m1 stop
$46Frontier
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Tue, Feb 11
6:00 am - 2:25 pmBOS-ORD
9h 25m1 stop
$53Frontier
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Wed, Feb 26
8:20 pm - 10:23 pmBOS-ORD
3h 03mnonstop
$79Delta
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Mon, Jan 27
5:50 pm - 10:57 pmBOS-ORD
6h 07m1 stop
$88United Airlines
Find Deal
Sat, Jan 18
11:45 am - 1:46 pmBOS-ORD
3h 01mnonstop
$89Delta
Find Deal
Wed, Feb 26
5:38 am - 10:59 amBOS-ORD
6h 21m1 stop
$98JetBlue
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Tue, Feb 25
10:00 am - 12:00 pmBOS-ORD
3h 00mnonstop
$104JetBlue
Find Deal
Wed, Feb 19
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$111United Airlines
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Tue, Dec 31
5:55 pm - 10:58 pmBOS-ORD
6h 03m1 stop
$133American Airlines
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Mon, Dec 30
6:25 am - 11:37 amBOS-ORD
6h 12m1 stop
$134American Airlines
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Sun, Jan 5
6:27 am - 7:19 pmBOS-ORD
13h 52m1 stop
4:28 pm - 12:41 amORD-BOS
7h 13m1 stop
Sat, Dec 28 - Mon, Jan 6
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
2:20 pm - 12:41 amMDW-BOS
9h 21m1 stop
$218Frontier
Find Deal
Fri, Dec 27 - Mon, Jan 6
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$252American Airlines
Find Deal
Tue, Dec 24 - Sun, Jan 12
10:00 am - 4:16 pmBOS-ORD
7h 16m1 stop
6:30 am - 10:03 amORD-BOS
2h 33mnonstop
$262American Airlines
Find Deal
Tue, Dec 24 - Sun, Jan 12
6:55 am - 12:32 pmBOS-ORD
6h 37m1 stop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$272Delta
Find Deal
Wed, Dec 25 - Tue, Jan 7
4:40 pm - 11:56 pmBOS-ORD
8h 16m1 stop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$283Delta
Find Deal
Tue, Dec 24 - Mon, Jan 6
4:07 pm - 6:10 pmBOS-ORD
3h 03mnonstop
8:37 am - 11:58 amORD-BOS
2h 21mnonstop
$297JetBlue
Find Deal
Thu, Dec 26 - Sun, Jan 5
6:00 am - 8:07 amBOS-ORD
3h 07mnonstop
6:55 pm - 10:21 pmORD-BOS
2h 26mnonstop
$327JetBlue
Find Deal
Sat, Dec 28 - Thu, Jan 2
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
6:08 pm - 11:59 pmORD-BOS
4h 51m1 stop
$342United Airlines
Find Deal
Fri, Dec 27 - Fri, Jan 10
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
9:20 am - 12:46 pmORD-BOS
2h 26mnonstop
$367United Airlines
Find Deal
Sat, Dec 28 - Thu, Jan 2
11:45 am - 1:50 pmBOS-ORD
3h 05mnonstop
2:35 pm - 6:10 pmORD-BOS
2h 35mnonstop
$155Delta
Find Deal
Tue, Jan 14 - Thu, Jan 16
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$157JetBlue
Find Deal
Sat, Jan 18 - Wed, Jan 22
6:35 pm - 8:25 pmBOS-MDW
2h 50mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$158Southwest
Find Deal
Thu, Jan 16 - Tue, Jan 21
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$158JetBlue
Find Deal
Sat, Jan 18 - Sun, Jan 19
8:45 am - 10:50 amBOS-ORD
3h 05mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$159American Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 19
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
6:45 pm - 10:12 pmORD-BOS
2h 27mnonstop
$160American Airlines
Find Deal
Mon, Jan 20 - Mon, Jan 27
8:10 am - 10:12 amBOS-ORD
3h 02mnonstop
9:05 am - 12:23 pmORD-BOS
2h 18mnonstop
$167JetBlue
Find Deal
Fri, Jan 10 - Tue, Jan 14
10:52 am - 12:54 pmBOS-ORD
3h 02mnonstop
6:35 pm - 9:59 pmORD-BOS
2h 24mnonstop
$177United Airlines
Find Deal
Thu, Feb 27 - Mon, Mar 3
8:05 pm - 9:55 pmBOS-MDW
2h 50mnonstop
7:45 am - 11:00 amMDW-BOS
2h 15mnonstop
$178Southwest
Find Deal
Thu, Mar 6 - Sat, Mar 8
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
6:30 pm - 9:59 pmORD-BOS
2h 29mnonstop
$212United Airlines
Find Deal
Thu, Jan 2 - Wed, Jan 8

American Airlines flights from Boston to Chicago

Our best American Airlines deals on Boston to Chicago flight tickets
American Airlines
Jan 18
BOS8:45 amBoston Logan Intl
3h 05m
ORD10:50 amChicago O'Hare Intl
Jan 19
ORD8:05 amChicago O'Hare Intl
2h 21m
BOS11:26 amBoston Logan Intl
American Airlines
Jan 20
BOS6:00 amBoston Logan Intl
3h 08m
ORD8:08 amChicago O'Hare Intl
Jan 27
ORD6:45 pmChicago O'Hare Intl
2h 27m
BOS10:12 pmBoston Logan Intl
American Airlines
Jan 11
BOS7:47 pmBoston Logan Intl
3h 09m
ORD9:56 pmChicago O'Hare Intl
Jan 12
ORD6:30 amChicago O'Hare Intl
2h 33m
BOS10:03 amBoston Logan Intl

Frontier flights from Boston to Chicago

Our best Frontier deals on Boston to Chicago flight tickets
Frontier
Feb 4
BOS6:00 amBoston Logan Intl
8h 36m
1 stop
ORD1:36 pmChicago O'Hare Intl
Feb 11
ORD2:59 pmChicago O'Hare Intl
8h 40m
1 stop
BOS12:39 amBoston Logan Intl
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 22
BOS6:00 amBoston Logan Intl
7h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl
Jan 28
ORD2:59 pmChicago O'Hare Intl
8h 40m
1 stop
BOS12:39 amBoston Logan Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Boston 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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $184. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $186.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $222. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Chicago for around $278.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $237. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $277.

What is the cheapest Boston Logan Intl to Chicago flight route?

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston Logan Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Boston is 57 days out, which is when prices tend to be around $244. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $167.

What cabin class options are available on Boston Logan Intl to Chicago flights?

There are 4 cabin classes available to choose from on Boston Logan Intl 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 Boston to Chicago flights?

You could potentially save up to 36% on your flight if you consider stops on a Boston to Chicago flight.

How have Boston to Chicago flight prices changed over time?

As of December 2024, prices for Boston to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

When to book flights from Boston to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Boston to Chicago (BOS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago

Best Price Found

$46

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Boston in the past 72 hours is $46. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $102.
The fastest flight from Boston to Chicago takes 2h 35m
Direct flights go from Boston to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • Is flying the fastest way to get from Boston to Chicago?

    To save time, the fastest way to travel is by flight from Boston to Chicago on Southwest. Expect the length of time you’ll spend onboard Southwest to be about 2h 40m compared to taking a train from Boston to Chicago or a bus from Boston to Chicago which have been found to be slower alternatives.

  • Is flying the cheapest way to get from Boston to Chicago?

    The cheapest way is to get a flight from Boston to Chicago, which can be as cheap as $102. A train from Boston to Chicago is more expensive than a flight, with prices starting at $262. A bus from Boston to Chicago is also an option, with an average price of $247.

  • How far is Boston Logan Intl to Chicago by plane?

    A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 40m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?

    Prices for flights from Boston Logan Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?

  • How old do you have to be to fly from Boston Logan Intl Airport to Chicago?

    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 Boston Logan Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago 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 Boston to Chicago?

  • What is the most popular airline from Boston to Chicago?


Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $39Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
JetBluePriceFrom $81Free CancellationRating
7.4
3,263 reviews
Search JetBlue flights
DeltaPriceFrom $93Free CancellationRating
8.0
8,588 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.1
3,469 reviews
Search Frontier flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
9,022 reviews
Search United Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.1
4,780 reviews
Search Southwest flights
  • Southwest Flights From Boston to Chicago

    The lowest priced Southwest flight from Boston to Chicago from the last 72 hours was $148. Generally, Southwest has 20 flights on this route every week with an average price of $294. Southwest is rated 8.1/10 by our users.

  • Delta Flights From Boston to Chicago

    Delta is also a popular choice for this route. Delta flight deals for Boston to Chicago start from as low as $93 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $345. Delta operates 13 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 8,588 reviews.


Why use momondo?

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

It is quick and easy to find Boston 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 Boston to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Boston to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Boston 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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago