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Cheap flights from Boston to Chicago from £62

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 15/1. 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.
06:00 - 13:34BOS-ORD
8h 34m1 stop
12:42 - 00:30ORD-BOS
10h 48m1 stop
£80Frontier
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Tue, 14 Jan - Wed, 15 Jan
06:00 - 09:52BOS-ORD
28h 52m1 stop
13:45 - 00:39ORD-BOS
9h 54m1 stop
£99Frontier
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Thu, 23 Jan - Wed, 5 Feb
08:10 - 10:12BOS-ORD
3h 02mdirect
09:05 - 12:23ORD-BOS
2h 18mdirect
£123JetBlue
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Thu, 9 Jan - Sun, 12 Jan
15:52 - 17:59BOS-ORD
3h 07mdirect
07:00 - 10:15ORD-BOS
2h 15mdirect
£124JetBlue
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Thu, 9 Jan - Sat, 11 Jan
12:12 - 14:10BOS-ORD
2h 58mdirect
13:15 - 19:00ORD-BOS
4h 45m1 stop
£132United Airlines
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Tue, 7 Jan - Fri, 10 Jan
19:42 - 23:25BOS-ORD
4h 43m1 stop
09:20 - 12:46ORD-BOS
2h 26mdirect
£144United Airlines
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Tue, 31 Dec - Wed, 8 Jan
20:20 - 22:19BOS-ORD
2h 59mdirect
14:35 - 18:06ORD-BOS
2h 31mdirect
£148Delta
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Mon, 24 Feb - Wed, 5 Mar
07:15 - 09:25BOS-ORD
3h 10mdirect
14:55 - 00:58ORD-BOS
9h 03m1 stop
£162Delta
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Wed, 22 Jan - Tue, 4 Feb
16:10 - 22:04BOS-ORD
6h 54m1 stop
20:20 - 23:44ORD-BOS
2h 24mdirect
£165American Airlines
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Tue, 14 Jan - Wed, 15 Jan
05:20 - 07:21BOS-ORD
3h 01mdirect
07:00 - 10:20ORD-BOS
2h 20mdirect
£185American Airlines
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Thu, 13 Feb - Mon, 24 Feb
06:10 - 08:14BOS-ORD
3h 04mdirect
£62JetBlue
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Wed, 15 Jan
15:52 - 17:55BOS-ORD
3h 03mdirect
£62JetBlue
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Wed, 5 Feb
15:10 - 17:10BOS-ORD
3h 00mdirect
£70Delta
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Tue, 18 Mar
16:17 - 22:00BOS-ORD
6h 43m1 stop
£74United Airlines
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Mon, 24 Mar
12:05 - 14:05BOS-ORD
3h 00mdirect
£75Delta
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Sat, 22 Feb
14:10 - 20:25BOS-ORD
7h 15m1 stop
£82United Airlines
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Wed, 25 Dec
06:55 - 16:45BOS-ORD
10h 50m2 stops
£113Southwest
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Wed, 5 Feb
06:55 - 16:45BOS-ORD
10h 50m2 stops
£114Southwest
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Wed, 19 Feb
17:55 - 13:07BOS-ORD
20h 12m2 stops
£150Alaska Airlines
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Tue, 28 Jan
07:00 - 13:07BOS-ORD
31h 07m2 stops
£156Alaska Airlines
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Sat, 18 Jan
15:05 - 22:52BOS-ORD
8h 47m1 stop
07:10 - 10:47ORD-BOS
2h 37mdirect
£223Delta
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Tue, 24 Dec - Mon, 6 Jan
16:25 - 18:25BOS-ORD
3h 00mdirect
07:30 - 10:56ORD-BOS
2h 26mdirect
£237United Airlines
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Sun, 22 Dec - Sun, 12 Jan
15:05 - 22:52BOS-ORD
8h 47m1 stop
07:35 - 11:03ORD-BOS
2h 28mdirect
£242Delta
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Tue, 24 Dec - Wed, 25 Dec
18:25 - 20:25BOS-ORD
3h 00mdirect
07:10 - 14:07ORD-BOS
5h 57m1 stop
£245United Airlines
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Sun, 22 Dec - Sun, 12 Jan
17:35 - 23:53BOS-ORD
7h 18m1 stop
18:25 - 22:08ORD-BOS
2h 43mdirect
£258Delta
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Sun, 22 Dec - Tue, 7 Jan
22:35 - 13:00BOS-ORD
15h 25m2 stops
07:00 - 17:00ORD-BOS
9h 00m1 stop
£265Southwest
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Mon, 23 Dec - Wed, 22 Jan
22:35 - 13:00BOS-ORD
15h 25m2 stops
11:25 - 22:30ORD-BOS
10h 05m2 stops
£269Southwest
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Mon, 23 Dec - Wed, 22 Jan
17:35 - 23:53BOS-ORD
7h 18m1 stop
07:35 - 11:03ORD-BOS
2h 28mdirect
£274Delta
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Sun, 22 Dec - Fri, 3 Jan
06:00 - 08:07BOS-ORD
3h 07mdirect
08:42 - 12:11ORD-BOS
2h 29mdirect
£278JetBlue
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Mon, 23 Dec - Wed, 25 Dec
06:00 - 08:07BOS-ORD
3h 07mdirect
08:42 - 12:11ORD-BOS
2h 29mdirect
£305JetBlue
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Sun, 22 Dec - Wed, 25 Dec
08:10 - 10:12BOS-ORD
3h 02mdirect
09:05 - 12:23ORD-BOS
2h 18mdirect
£123JetBlue
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Thu, 9 Jan - Sun, 12 Jan
15:52 - 17:59BOS-ORD
3h 07mdirect
07:00 - 10:15ORD-BOS
2h 15mdirect
£124JetBlue
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Thu, 9 Jan - Sun, 19 Jan
15:52 - 17:59BOS-ORD
3h 07mdirect
07:00 - 10:15ORD-BOS
2h 15mdirect
£132JetBlue
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Tue, 7 Jan - Thu, 9 Jan
08:10 - 10:12BOS-ORD
3h 02mdirect
09:05 - 12:23ORD-BOS
2h 18mdirect
£136JetBlue
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Mon, 10 Feb - Sat, 15 Feb
13:41 - 15:40BOS-ORD
2h 59mdirect
13:00 - 16:20ORD-BOS
2h 20mdirect
£140JetBlue
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Tue, 25 Feb - Thu, 6 Mar
11:45 - 13:50BOS-ORD
3h 05mdirect
07:10 - 10:47ORD-BOS
2h 37mdirect
£147Delta
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Wed, 15 Jan - Mon, 20 Jan
06:02 - 08:05BOS-ORD
3h 03mdirect
14:00 - 17:23ORD-BOS
2h 23mdirect
£150United Airlines
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Tue, 31 Dec - Wed, 8 Jan
10:57 - 12:55BOS-ORD
2h 58mdirect
09:20 - 12:46ORD-BOS
2h 26mdirect
£155United Airlines
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Thu, 16 Jan - Mon, 20 Jan
11:45 - 13:50BOS-ORD
3h 05mdirect
07:10 - 10:47ORD-BOS
2h 37mdirect
£159Delta
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Wed, 15 Jan - Mon, 20 Jan
05:20 - 07:21BOS-ORD
3h 01mdirect
07:00 - 10:20ORD-BOS
2h 20mdirect
£185American Airlines
Find Deal
Thu, 13 Feb - Mon, 24 Feb

United Airlines flights from Boston to Chicago

Our best United Airlines deals on Boston to Chicago flight tickets
United Airlines
7 Jan
BOS12:12Boston Logan Intl
2h 58m
ORD14:10Chicago O'Hare Intl
10 Jan
ORD13:15Chicago O'Hare Intl
4h 45m
1 stop
BOS19:00Boston Logan Intl
United Airlines
31 Dec
BOS19:42Boston Logan Intl
4h 43m
1 stop
ORD23:25Chicago O'Hare Intl
8 Jan
ORD09:20Chicago O'Hare Intl
2h 26m
BOS12:46Boston Logan Intl
United Airlines
31 Dec
BOS06:02Boston Logan Intl
3h 03m
ORD08:05Chicago O'Hare Intl
7 Jan
ORD07:30Chicago O'Hare Intl
2h 26m
BOS10:56Boston Logan Intl

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
24 Feb
BOS20:20Boston Logan Intl
2h 59m
ORD22:19Chicago O'Hare Intl
5 Mar
ORD14:35Chicago O'Hare Intl
2h 31m
BOS18:06Boston Logan Intl
Delta
22 Jan
BOS07:15Boston Logan Intl
3h 10m
ORD09:25Chicago O'Hare Intl
4 Feb
ORD14:55Chicago O'Hare Intl
9h 03m
1 stop
BOS00:58Boston Logan Intl
Delta
24 Apr
BOS07:00Boston Logan Intl
3h 01m
ORD09:01Chicago O'Hare Intl
28 Apr
ORD06:30Chicago O'Hare Intl
2h 26m
BOS09:56Boston 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 cheapest month to fly to Chicago from Boston is in September. Flight prices, which tend to average around £145, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Boston during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £147.

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 Monday when prices can be found for as low as £0. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £132.

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

Flying to Chicago from Boston at midday is the least expensive time of day to depart. momondo users have found prices as low as £0 when looking at flights departing at midday. Flights in the evening are often more expensive, with an average ticket price of £170.

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 ideal time to book your flight to Chicago is 57 days in advance, when prices tend to average £192. However, in the past 72 hours, people saw flights from Boston for as low as £104.

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

There are 3 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 12% 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 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

£62

Fastest flight time

2h 52m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Boston in the past 72 hours is £62. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £80.
The fastest flight from Boston to Chicago takes 2h 52m
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 28m 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 £80. 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 52m 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 50m
£91 one-way£205 return
Direct · from £205

Distance to city centre

F990.8 mi

Find Buses

Boston to Chicago Buses

Trains

22h 15m
£85 one-way£222 return
Direct · from £222

Distance to city centre

ZUN0.7 mi

Find Trains

Boston to Chicago Trains

Flights

2h 53m
£62 one-way£80 return
Direct · from £1231 stop · from £131

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