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Cheap flights from Boston to Chicago from £48

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 4/12. 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 return flights

These are some of the best return 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 stopovers.

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.
12:59 - 22:38BOS-ORD
10h 39m1 stop
15:25 - 00:30ORD-BOS
8h 05m1 stop
£86Frontier
Find Deal
Mon, 9 Dec - Mon, 16 Dec
08:54 - 15:43BOS-ORD
7h 49m1 stop
22:15 - 07:33ORD-BOS
8h 18m1 stop
£97Frontier
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Mon, 16 Dec - Thu, 19 Dec
06:00 - 07:56BOS-ORD
2h 56mdirect
09:20 - 12:45ORD-BOS
2h 25mdirect
£124United Airlines
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Thu, 5 Dec - Sun, 8 Dec
15:52 - 17:59BOS-ORD
3h 07mdirect
07:00 - 10:15ORD-BOS
2h 15mdirect
£125JetBlue
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Thu, 9 Jan - Sun, 12 Jan
06:00 - 08:06BOS-ORD
3h 06mdirect
10:14 - 15:43ORD-BOS
4h 29m1 stop
£127JetBlue
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Tue, 10 Dec - Tue, 10 Dec
11:05 - 13:00BOS-ORD
2h 55mdirect
06:30 - 10:00ORD-BOS
2h 30mdirect
£130Delta
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Thu, 12 Dec - Fri, 13 Dec
11:05 - 13:03BOS-ORD
2h 58mdirect
10:30 - 13:52ORD-BOS
2h 22mdirect
£133Delta
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Thu, 5 Dec - Mon, 9 Dec
05:00 - 16:06BOS-ORD
12h 06m1 stop
17:11 - 14:56ORD-BOS
20h 45m2 stops
£135Spirit Airlines
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Tue, 10 Dec - Wed, 11 Dec
06:02 - 08:05BOS-ORD
3h 03mdirect
06:00 - 12:07ORD-BOS
5h 07m1 stop
£144United Airlines
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Wed, 1 Jan - Mon, 20 Jan
20:30 - 16:06BOS-ORD
20h 36m2 stops
13:24 - 23:15ORD-BOS
8h 51m1 stop
£158Spirit Airlines
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Mon, 16 Dec - Thu, 19 Dec
06:00 - 08:24BOS-ORD
27h 24m1 stop
£48Frontier
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Wed, 4 Dec
11:05 - 13:00BOS-ORD
2h 55mdirect
£62Delta
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Sun, 15 Dec
11:28 - 15:44BOS-ORD
5h 16m1 stop
£69JetBlue
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Sun, 19 Jan
13:59 - 15:53BOS-ORD
2h 54mdirect
£70JetBlue
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Tue, 3 Dec
06:02 - 08:05BOS-ORD
3h 03mdirect
£75United Airlines
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Tue, 31 Dec
06:02 - 08:05BOS-ORD
3h 03mdirect
£87United Airlines
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Wed, 25 Dec
05:45 - 11:30BOS-ORD
6h 45m1 stop
£93Southwest
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Sun, 19 Jan
06:55 - 16:45BOS-ORD
10h 50m2 stops
£97Southwest
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Wed, 5 Feb
17:55 - 13:07BOS-ORD
20h 12m2 stops
£159Alaska Airlines
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Tue, 14 Jan
07:00 - 13:07BOS-ORD
31h 07m2 stops
£183Alaska Airlines
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Thu, 23 Jan
19:50 - 21:51BOS-ORD
3h 01mdirect
06:40 - 10:00ORD-BOS
2h 20mdirect
£167Delta
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Mon, 25 Nov - Thu, 5 Dec
06:00 - 07:56BOS-ORD
2h 56mdirect
15:35 - 18:56ORD-BOS
2h 21mdirect
£172United Airlines
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Mon, 25 Nov - Tue, 26 Nov
06:00 - 07:56BOS-ORD
2h 56mdirect
10:37 - 14:02ORD-BOS
2h 25mdirect
£199United Airlines
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Sun, 24 Nov - Wed, 4 Dec
15:45 - 17:46BOS-ORD
3h 01mdirect
06:40 - 10:00ORD-BOS
2h 20mdirect
£207Delta
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Mon, 25 Nov - Wed, 4 Dec
13:59 - 15:53BOS-ORD
2h 54mdirect
08:50 - 12:12ORD-BOS
2h 22mdirect
£223JetBlue
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Fri, 22 Nov - Wed, 4 Dec
13:59 - 15:53BOS-ORD
2h 54mdirect
12:15 - 15:28ORD-BOS
2h 13mdirect
£234JetBlue
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Thu, 21 Nov - Wed, 27 Nov
08:25 - 14:00BOS-ORD
6h 35m1 stop
05:45 - 11:25ORD-BOS
4h 40m1 stop
£254Southwest
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Sun, 24 Nov - Mon, 25 Nov
10:45 - 22:00BOS-ORD
12h 15m2 stops
14:55 - 00:05ORD-BOS
8h 10m2 stops
£273Southwest
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Mon, 25 Nov - Wed, 27 Nov
08:27 - 05:28BOS-ORD
22h 01m2 stops
07:00 - 00:59ORD-BOS
16h 59m2 stops
£737Alaska Airlines
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Sat, 23 Nov - Wed, 27 Nov
08:27 - 05:28BOS-ORD
22h 01m2 stops
07:00 - 05:47ORD-BOS
21h 47m2 stops
£895Alaska Airlines
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Sat, 23 Nov - Mon, 25 Nov
06:00 - 07:56BOS-ORD
2h 56mdirect
09:20 - 12:45ORD-BOS
2h 25mdirect
£124United Airlines
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Thu, 5 Dec - Sun, 8 Dec
15:52 - 17:59BOS-ORD
3h 07mdirect
07:00 - 10:15ORD-BOS
2h 15mdirect
£125JetBlue
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Thu, 9 Jan - Sun, 12 Jan
11:05 - 13:00BOS-ORD
2h 55mdirect
06:30 - 10:00ORD-BOS
2h 30mdirect
£130Delta
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Thu, 12 Dec - Fri, 13 Dec
13:59 - 15:53BOS-ORD
2h 54mdirect
08:50 - 12:12ORD-BOS
2h 22mdirect
£132JetBlue
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Tue, 3 Dec - Wed, 4 Dec
15:45 - 17:46BOS-ORD
3h 01mdirect
06:30 - 10:00ORD-BOS
2h 30mdirect
£133Delta
Find Deal
Thu, 5 Dec - Mon, 9 Dec
11:05 - 13:00BOS-ORD
2h 55mdirect
07:35 - 11:03ORD-BOS
2h 28mdirect
£137Delta
Find Deal
Tue, 17 Dec - Tue, 24 Dec
07:25 - 09:28BOS-ORD
3h 03mdirect
10:40 - 14:13ORD-BOS
2h 33mdirect
£140Delta
Find Deal
Wed, 18 Dec - Tue, 7 Jan
06:00 - 08:07BOS-ORD
3h 07mdirect
09:05 - 12:23ORD-BOS
2h 18mdirect
£141JetBlue
Find Deal
Mon, 6 Jan - Sat, 11 Jan
06:00 - 08:07BOS-ORD
3h 07mdirect
07:00 - 10:15ORD-BOS
2h 15mdirect
£144JetBlue
Find Deal
Sat, 4 Jan - Wed, 8 Jan
10:45 - 12:41BOS-ORD
2h 56mdirect
09:20 - 12:45ORD-BOS
2h 25mdirect
£145United Airlines
Find Deal
Tue, 3 Dec - Thu, 5 Dec

Frontier flights from Boston to Chicago

Our best Frontier deals on Boston to Chicago flight tickets
Frontier
9 Dec
BOS12:59Boston Logan Intl
10h 39m
1 stop
ORD22:38Chicago O'Hare Intl
16 Dec
ORD15:25Chicago O'Hare Intl
8h 05m
1 stop
BOS00:30Boston Logan Intl
Frontier
16 Dec
BOS08:54Boston Logan Intl
7h 49m
1 stop
ORD15:43Chicago O'Hare Intl
19 Dec
ORD22:15Chicago O'Hare Intl
8h 18m
1 stop
BOS07:33Boston Logan Intl

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
9 Jan
BOS15:52Boston Logan Intl
3h 07m
ORD17:59Chicago O'Hare Intl
12 Jan
ORD07:00Chicago O'Hare Intl
2h 15m
BOS10:15Boston Logan Intl
JetBlue
10 Dec
BOS06:00Boston Logan Intl
3h 06m
ORD08:06Chicago O'Hare Intl
10 Dec
ORD10:14Chicago O'Hare Intl
4h 29m
1 stop
BOS15:43Boston Logan Intl
JetBlue
10 Jan
BOS11:28Boston Logan Intl
5h 16m
1 stop
ORD15:44Chicago O'Hare Intl
14 Jan
ORD07:00Chicago O'Hare Intl
2h 15m
BOS10:15Boston 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. The most expensive is April.

What is the cheapest day to depart Boston for Chicago?

Friday. The cheapest day of the week is usually Friday. The most expensive is usually Thursday.

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

In the morning. Boston to Chicago flights are approximately 3% more expensive in the evening than in the morning

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?

36 flights are operational weekly from Boston to Chicago as of November 2024. The most popular departure time for this route is 06:00, with 43% of flights per day taking off at midday.

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

The number of flights available between Boston and Chicago is 254 per week as of November 2024. The most frequent departure day is Tue, with 20% of weekly flights leaving on this day.

Can stopping save me money on Boston to Chicago flights?

You could potentially save up to 21% 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 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 return 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

£48

Fastest flight time

2h 44m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Boston in the past 72 hours is £48. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £86.
The fastest flight from Boston to Chicago takes 2h 44m
Direct flights go from Boston to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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

    The quickest way to travel this route is to take a flight from Boston to Chicago, doing so can potentially save up to 25h 05m of travel time. While these options may take longer, booking a train from Boston to Chicago or a bus from Boston to Chicago may suit your needs if travel time is less of a factor in your decision making.

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

    Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from £86. While they may not be the most cost-effective options currently available a train from Boston to Chicago or a bus from Boston to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

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

    Chicago is 847.9 mi away from Boston Logan Intl. 2h 50m 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 were last updated today.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Boston to Chicago?


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?

Flights from Boston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Boston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Boston 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 Boston and alert you when they change.


Choose the best way to get from Boston to Chicago

Buses

27h 55m
£128 one-way£284 return
Direct · from £284

Distance to city centre

G1N10.6 mi
F990.8 mi

Find Buses

Boston to Chicago Buses

Trains

22h 15m
£86 one-way£190 return
Direct · from £190

Distance to city centre

ZUN0.7 mi

Find Trains

Boston to Chicago Trains

Flights

2h 44m
£48 one-way£86 return
Direct · from £1241 stop · from £127

Distance to city centre

ORD15.9 mi

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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