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Cheap flights from Boston to Chicago from $49

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 12/4. 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 - 11:42 amBOS-MDW
6h 42m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$101Frontier
Find Deal
Wed, Dec 4 - Tue, Dec 10
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
2:20 pm - 12:30 amMDW-BOS
9h 10m1 stop
$104Frontier
Find Deal
Tue, Dec 10 - Wed, Dec 18
11:05 am - 1:03 pmBOS-ORD
2h 58mnonstop
6:50 pm - 10:22 pmORD-BOS
2h 32mnonstop
$156Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
3:40 pm - 5:36 pmBOS-ORD
2h 56mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$157Delta
Find Deal
Fri, Dec 6 - Mon, Dec 9
5:01 am - 9:01 amBOS-ORD
5h 00m1 stop
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
$166JetBlue
Find Deal
Thu, Nov 21 - Wed, Dec 4
9:30 am - 11:26 amBOS-ORD
2h 56mnonstop
6:00 am - 12:06 pmORD-BOS
5h 06m1 stop
$167United Airlines
Find Deal
Fri, Dec 6 - Wed, Dec 11
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
10:14 am - 3:43 pmORD-BOS
4h 29m1 stop
$171JetBlue
Find Deal
Sat, Dec 7 - Sat, Dec 7
6:55 pm - 11:00 pmBOS-ORD
5h 05m1 stop
6:16 pm - 11:59 pmORD-BOS
4h 43m1 stop
$176United Airlines
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Thu, Dec 5 - Fri, Dec 6
5:00 am - 7:04 amBOS-ORD
3h 04mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$199American Airlines
Find Deal
Sun, Dec 29 - Sat, Jan 4
6:40 am - 10:57 amBOS-ORD
5h 17m1 stop
8:12 am - 11:27 amORD-BOS
2h 15mnonstop
$207American Airlines
Find Deal
Thu, Dec 5 - Sun, Dec 8
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$49Frontier
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Wed, Dec 4
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$50Frontier
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Tue, Dec 10
12:00 pm - 2:01 pmBOS-ORD
3h 01mnonstop
$76American Airlines
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Wed, Nov 20
3:50 pm - 5:53 pmBOS-ORD
3h 03mnonstop
$79JetBlue
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Wed, Feb 5
11:25 am - 3:28 pmBOS-ORD
5h 03m1 stop
$88JetBlue
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Thu, Jan 9
9:00 am - 11:03 amBOS-ORD
3h 03mnonstop
$100Delta
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Fri, Jan 3
5:45 am - 9:55 amBOS-ORD
5h 10m1 stop
$109United Airlines
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Wed, Dec 25
3:45 pm - 5:46 pmBOS-ORD
3h 01mnonstop
$124Delta
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Wed, Nov 13
7:00 am - 12:25 pmBOS-ORD
6h 25m1 stop
$128American Airlines
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Thu, Nov 28
5:45 am - 9:55 amBOS-ORD
5h 10m1 stop
$131United Airlines
Find Deal
Sun, Dec 29
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
7:46 pm - 9:24 amORD-BOS
12h 38m1 stop
$120Spirit Airlines
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Tue, Nov 12 - Wed, Nov 13
9:39 am - 4:56 pmBOS-ORD
8h 17m1 stop
4:38 pm - 7:57 pmORD-BOS
2h 19mnonstop
Tue, Nov 12 - Fri, Nov 15
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
4:53 pm - 8:14 pmORD-BOS
2h 21mnonstop
$247JetBlue
Find Deal
Tue, Nov 12 - Wed, Nov 13
5:01 am - 9:03 amBOS-ORD
5h 02m1 stop
6:00 am - 9:17 amORD-BOS
2h 17mnonstop
$291JetBlue
Find Deal
Mon, Nov 11 - Sat, Nov 23
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
12:45 pm - 6:33 pmORD-BOS
4h 48m1 stop
$307United Airlines
Find Deal
Sat, Nov 9 - Wed, Nov 13
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
$311United Airlines
Find Deal
Mon, Nov 11 - Tue, Nov 12
8:30 am - 1:10 pmBOS-ORD
5h 40m1 stop
6:30 am - 12:16 pmORD-BOS
4h 46m1 stop
$316American Airlines
Find Deal
Sat, Nov 9 - Thu, Nov 14
7:40 pm - 9:32 pmBOS-ORD
2h 52mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$322Delta
Find Deal
Sat, Nov 9 - Tue, Nov 12
5:20 am - 8:50 amBOS-MDW
4h 30m1 stop
1:30 pm - 8:00 pmMDW-BOS
5h 30m1 stop
$326Delta
Find Deal
Tue, Nov 12 - Tue, Nov 12
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$342American Airlines
Find Deal
Mon, Nov 11 - Tue, Nov 26
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$116Spirit Airlines
Find Deal
Sun, Nov 24 - Mon, Nov 25
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$119Spirit Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
11:05 am - 1:03 pmBOS-ORD
2h 58mnonstop
6:50 pm - 10:22 pmORD-BOS
2h 32mnonstop
$156Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
6:59 pm - 9:06 pmBOS-ORD
3h 07mnonstop
6:00 am - 9:17 amORD-BOS
2h 17mnonstop
$157JetBlue
Find Deal
Thu, Nov 21 - Sun, Nov 24
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$158Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
9:30 am - 11:27 amBOS-ORD
2h 57mnonstop
6:00 am - 9:17 amORD-BOS
2h 17mnonstop
$167JetBlue
Find Deal
Fri, Nov 22 - Tue, Nov 26
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
4:15 pm - 7:38 pmORD-BOS
2h 23mnonstop
$178United Airlines
Find Deal
Sat, Jan 4 - Thu, Jan 9
10:57 am - 12:55 pmBOS-ORD
2h 58mnonstop
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
$184United Airlines
Find Deal
Fri, Jan 17 - Mon, Jan 20
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
8:20 pm - 11:44 pmORD-BOS
2h 24mnonstop
$187American Airlines
Find Deal
Thu, Nov 21 - Fri, Nov 22
6:30 am - 8:36 amBOS-ORD
3h 06mnonstop
7:25 am - 10:59 amORD-BOS
2h 34mnonstop
$188American Airlines
Find Deal
Wed, Dec 18 - Wed, Dec 25

Spirit Airlines flights from Boston to Chicago

Our best Spirit Airlines deals on Boston to Chicago flight tickets
Spirit Airlines
Nov 13
BOS6:00 amBoston Logan Intl
13h 41m
1 stop
ORD6:41 pmChicago O'Hare Intl
Nov 18
ORD4:38 pmChicago O'Hare Intl
2h 19m
BOS7:57 pmBoston Logan Intl
Spirit Airlines
Nov 19
BOS7:40 amBoston Logan Intl
3h 10m
ORD9:50 amChicago O'Hare Intl
Nov 24
ORD4:45 pmChicago O'Hare Intl
2h 19m
BOS8:04 pmBoston Logan Intl
Spirit Airlines
Nov 23
BOS7:48 amBoston Logan Intl
15h 18m
2 stops
ORD10:06 pmChicago O'Hare Intl
Nov 28
ORD4:45 pmChicago O'Hare Intl
2h 19m
BOS8:04 pmBoston Logan Intl

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
Nov 22
BOS11:05 amBoston Logan Intl
2h 58m
ORD1:03 pmChicago O'Hare Intl
Nov 25
ORD6:50 pmChicago O'Hare Intl
2h 32m
BOS10:22 pmBoston Logan Intl
Delta
Dec 6
BOS3:40 pmBoston Logan Intl
2h 56m
ORD5:36 pmChicago O'Hare Intl
Dec 9
ORD6:30 amChicago O'Hare Intl
2h 30m
BOS10:00 amBoston Logan Intl
Delta
Nov 22
BOS7:20 amBoston Logan Intl
3h 09m
ORD9:29 amChicago O'Hare Intl
Nov 25
ORD6:40 amChicago O'Hare Intl
2h 20m
BOS10:00 amBoston Logan Intl

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 from Boston to Chicago?

September. The cheapest time of year to fly to Chicago from Boston is September. Most expensive is April

What is the cheapest day to depart Boston for Chicago?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Boston to Chicago?

In the evening. Boston to Chicago flights are approximately 16% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago from Boston?

Spirit Airlines. Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from Boston to Chicago

What is the cheapest Boston to Chicago flight route?

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

How far in advance should you book Boston to Chicago flights?

23 days before. The cheapest time to buy a flight from Boston to Chicago is approximately 23 days to departure

How many flights depart from Boston to Chicago on average per day?

38 flights are operational weekly from Boston to Chicago as of November 2024. The most popular departure time for this route is 6:00AM, with 44% of flights per day taking off in the afternoon.

How many flights depart from Boston to Chicago on average per week?

As of November 2024, 270 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Thursday, with 23% of weekly flights taking off on this day.

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

There are 4 cabin classes available to choose from on Boston 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?

No. A direct flight is the cheapest option for a flight between Boston to Chicago.

How have Boston to Chicago flight prices changed over time?

As of November 2024, prices for Boston to Chicago flights are approximately 19% cheaper 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

$49

Fastest flight time

2h 45m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Boston in the past 72 hours is $49. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $101.
The fastest flight from Boston to Chicago takes 2h 45m
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 45m 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 $101. A train from Boston to Chicago is more expensive than a flight, with prices starting at $291. A bus from Boston to Chicago is also an option, with an average price of $428.

  • 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 45m 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
8,175 reviews
Search Spirit Airlines flights
JetBluePriceFrom $84Free CancellationRating
7.5
3,477 reviews
Search JetBlue flights
FrontierPriceFrom $90Free CancellationRating
6.1
3,567 reviews
Search Frontier flights
DeltaPriceFrom $94Free CancellationRating
8.0
8,828 reviews
Search Delta flights
American AirlinesPriceFrom $126Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $143Free CancellationRating
8.1
5,083 reviews
Search Southwest flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
9,206 reviews
Search United Airlines flights
  • Southwest Flights From Boston to Chicago

    The lowest priced Southwest flight from Boston to Chicago from the last 72 hours was $143. Generally, Southwest has 16 flights on this route every week with an average price of $230. 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 $94 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $348. Delta operates 7 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 8,828 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.


Choose the best way to get from Boston to Chicago

Buses

27h 55m
$132 one-way$428 round-trip
Nonstop · from $428

Distance to downtown

ZUN0.7 mi
F990.8 mi

Find Buses

Boston to Chicago Buses

Trains

22h 15m
$109 one-way$241 round-trip
Nonstop · from $241

Distance to downtown

ZUN0.7 mi

Flights

2h 45m
$49 one-way$101 round-trip
1 stop · from $116

Distance to downtown

MDW8.6 mi

An easier way to manage your Chicago trip

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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