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Cheap flights from Chicago to Boston from £59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 19/12. 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 Chicago to Boston

Cheap return flights

These are some of the best return flight deals from Chicago to Boston 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 Chicago to Boston.

Cheap last-minute flights

Planning a quick getaway from Chicago to Boston? 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 Boston, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Chicago to Boston

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

All round-trip flight deals to Boston

The cheapest plane tickets to Boston found on KAYAK recently.
09:58 - 00:38ORD-BOS
13h 40m1 stop
10:34 - 21:07BOS-ORD
11h 33m1 stop
£84Spirit Airlines
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Tue, 10 Dec - Wed, 11 Dec
10:25 - 13:55ORD-BOS
2h 30mdirect
15:45 - 17:46BOS-ORD
3h 01mdirect
£122Delta
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Wed, 4 Dec - Thu, 5 Dec
08:38 - 11:59ORD-BOS
2h 21mdirect
13:59 - 15:53BOS-ORD
2h 54mdirect
£124JetBlue
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Tue, 10 Dec - Wed, 11 Dec
10:14 - 15:43ORD-BOS
4h 29m1 stop
06:00 - 08:06BOS-ORD
3h 06mdirect
£131JetBlue
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Tue, 10 Dec - Wed, 11 Dec
08:48 - 14:32ORD-BOS
4h 44m1 stop
06:00 - 07:56BOS-ORD
2h 56mdirect
£132United Airlines
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Thu, 12 Dec - Sun, 15 Dec
15:50 - 19:11ORD-BOS
2h 21mdirect
19:42 - 23:25BOS-ORD
4h 43m1 stop
£144United Airlines
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Wed, 11 Dec - Wed, 25 Dec
13:30 - 19:50ORD-BOS
5h 20m1 stop
07:20 - 22:20BOS-ORD
16h 00m2 stops
£198Southwest
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Sat, 11 Jan - Thu, 16 Jan
11:55 - 10:41ORD-BOS
21h 46m1 stop
11:46 - 10:31BOS-ORD
23h 45m1 stop
£209Sun Country Air
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Fri, 13 Dec - Mon, 16 Dec
05:45 - 17:45ORD-BOS
11h 00m1 stop
05:40 - 21:30BOS-ORD
16h 50m2 stops
£211Southwest
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Sun, 8 Dec - Thu, 12 Dec
12:22 - 10:41ORD-BOS
21h 19m1 stop
11:37 - 10:38BOS-ORD
24h 01m1 stop
£225Sun Country Air
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Thu, 12 Dec - Sun, 15 Dec
22:15 - 07:33ORD-BOS
8h 18m1 stop
£59Frontier
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Thu, 19 Dec
06:30 - 10:00ORD-BOS
2h 30mdirect
£62Delta
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Wed, 18 Dec
13:55 - 17:16ORD-BOS
2h 21mdirect
£62United Airlines
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Tue, 10 Dec
06:00 - 12:05ORD-BOS
5h 05m1 stop
£69United Airlines
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Sun, 16 Feb
07:00 - 10:15ORD-BOS
2h 15mdirect
£70JetBlue
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Sun, 2 Feb
17:40 - 00:18ORD-BOS
5h 38m1 stop
£77JetBlue
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Fri, 14 Feb
20:14 - 09:58ORD-BOS
12h 44m1 stop
£84Spirit Airlines
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Fri, 20 Dec
20:02 - 09:33ORD-BOS
12h 31m1 stop
£108Spirit Airlines
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Mon, 2 Dec
05:45 - 22:10ORD-BOS
15h 25m3 stops
£109Southwest
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Wed, 18 Dec
11:25 - 22:30ORD-BOS
10h 05m2 stops
£121Southwest
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Mon, 3 Feb
16:45 - 20:04ORD-BOS
2h 19mdirect
20:59 - 09:06BOS-ORD
13h 07m1 stop
£221Spirit Airlines
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Sat, 23 Nov - Mon, 25 Nov
21:35 - 00:54ORD-BOS
2h 19mdirect
20:32 - 22:28BOS-ORD
2h 56mdirect
£234United Airlines
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Mon, 25 Nov - Sun, 1 Dec
06:00 - 09:17ORD-BOS
2h 17mdirect
05:01 - 09:01BOS-ORD
5h 00m1 stop
£242JetBlue
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Fri, 22 Nov - Tue, 26 Nov
11:22 - 17:52ORD-BOS
5h 30m1 stop
11:05 - 13:03BOS-ORD
2h 58mdirect
£242Delta
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Sat, 23 Nov - Tue, 3 Dec
16:39 - 20:01ORD-BOS
2h 22mdirect
20:55 - 22:42BOS-ORD
2h 47mdirect
£246JetBlue
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Sat, 23 Nov - Wed, 27 Nov
17:55 - 23:49ORD-BOS
4h 54m1 stop
11:05 - 13:03BOS-ORD
2h 58mdirect
£262Delta
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Fri, 22 Nov - Tue, 3 Dec
05:45 - 15:25ORD-BOS
8h 40m1 stop
10:45 - 22:00BOS-ORD
12h 15m2 stops
£285Southwest
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Thu, 21 Nov - Mon, 25 Nov
12:15 - 00:10ORD-BOS
10h 55m2 stops
05:25 - 14:00BOS-ORD
9h 35m1 stop
£297Southwest
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Sat, 23 Nov - Wed, 27 Nov
07:00 - 00:59ORD-BOS
16h 59m2 stops
07:07 - 13:29BOS-ORD
31h 22m2 stops
£575Alaska Airlines
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Mon, 25 Nov - Thu, 28 Nov
14:15 - 15:00ORD-BOS
23h 45m2 stops
07:07 - 04:30BOS-ORD
22h 23m2 stops
£689Alaska Airlines
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Sat, 23 Nov - Wed, 27 Nov
10:25 - 13:55ORD-BOS
2h 30mdirect
15:45 - 17:46BOS-ORD
3h 01mdirect
£122Delta
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Wed, 4 Dec - Thu, 5 Dec
08:38 - 11:59ORD-BOS
2h 21mdirect
13:59 - 15:53BOS-ORD
2h 54mdirect
£124JetBlue
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Tue, 10 Dec - Wed, 11 Dec
06:40 - 10:00ORD-BOS
2h 20mdirect
07:25 - 09:28BOS-ORD
3h 03mdirect
£125Delta
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Thu, 5 Dec - Sun, 8 Dec
06:30 - 10:00ORD-BOS
2h 30mdirect
15:40 - 17:36BOS-ORD
2h 56mdirect
£130Delta
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Sun, 8 Dec - Wed, 11 Dec
08:51 - 12:13ORD-BOS
2h 22mdirect
06:00 - 08:06BOS-ORD
3h 06mdirect
£132JetBlue
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Wed, 11 Dec - Wed, 18 Dec
06:40 - 10:00ORD-BOS
2h 20mdirect
07:25 - 09:28BOS-ORD
3h 03mdirect
£133Delta
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Thu, 5 Dec - Sun, 8 Dec
07:35 - 11:03ORD-BOS
2h 28mdirect
11:45 - 13:50BOS-ORD
3h 05mdirect
£137Delta
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Wed, 25 Dec - Tue, 7 Jan
10:55 - 14:22ORD-BOS
2h 27mdirect
06:02 - 08:05BOS-ORD
3h 03mdirect
£156United Airlines
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Thu, 19 Dec - Wed, 1 Jan
07:30 - 10:49ORD-BOS
2h 19mdirect
18:28 - 20:24BOS-ORD
2h 56mdirect
£158United Airlines
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Fri, 6 Dec - Fri, 6 Dec
06:00 - 09:23ORD-BOS
2h 23mdirect
21:31 - 23:15BOS-ORD
2h 44mdirect
£163United Airlines
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Tue, 15 Apr - Tue, 22 Apr

Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets
Southwest
11 Jan
ORD13:30Chicago O'Hare Intl
5h 20m
1 stop
BOS19:50Boston Logan Intl
16 Jan
BOS07:20Boston Logan Intl
16h 00m
2 stops
ORD22:20Chicago O'Hare Intl
Southwest
8 Dec
ORD05:45Chicago O'Hare Intl
11h 00m
1 stop
BOS17:45Boston Logan Intl
12 Dec
BOS05:40Boston Logan Intl
16h 50m
2 stops
ORD21:30Chicago O'Hare Intl
Southwest
29 Jan
ORD11:25Chicago O'Hare Intl
10h 05m
2 stops
BOS22:30Boston Logan Intl
2 Feb
BOS15:35Boston Logan Intl
7h 45m
2 stops
ORD22:20Chicago O'Hare Intl

Sun Country Air flights from Chicago to Boston

Our best Sun Country Air deals on Chicago to Boston flight tickets
Sun Country Air
13 Dec
ORD11:55Chicago O'Hare Intl
21h 46m
1 stop
BOS10:41Boston Logan Intl
16 Dec
BOS11:46Boston Logan Intl
23h 45m
1 stop
ORD10:31Chicago O'Hare Intl
Sun Country Air
12 Dec
ORD12:22Chicago O'Hare Intl
21h 19m
1 stop
BOS10:41Boston Logan Intl
15 Dec
BOS11:37Boston Logan Intl
24h 01m
1 stop
ORD10:38Chicago O'Hare Intl

See travel insights to Boston from

How to get the cheapest flight ticket from Chicago to Boston

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 Chicago to Boston?

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

What is the cheapest day to depart Chicago for Boston?

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

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

In the afternoon. Chicago to Boston flights are approximately 36% more expensive in the morning than in the afternoon

What is the cheapest Chicago to Boston flight route?

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

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

35 days before. The cheapest time to buy a flight from Chicago to Boston is approximately 35 days to departure

Can stopping save me money on Chicago to Boston flights?

You could potentially save up to 3% on your flight if you consider stops on a Chicago to Boston flight.

How have Chicago to Boston flight prices changed over time?

As of November 2024, prices for Chicago to Boston flights are approximately 14% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Boston

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

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

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

Best price found

£59

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is £59. The best return flight deal from Chicago to Boston found on momondo in the last 72 hours is £84.
The fastest flight from Chicago to Boston takes 2h 15m
Direct flights go from Chicago to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)

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

    The quickest way to travel this route is to take a flight from Chicago to Boston, doing so can potentially save up to 23h 20m of travel time. While these options may take longer, booking a train from Chicago to Boston or a bus from Chicago to Boston may suit your needs if travel time is less of a factor in your decision making.

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

    A flight from Chicago to Boston is currently going to be the least expensive option currently available. You can also find deals for a train from Chicago to Boston starting at £208, or consider a bus from Chicago to Boston starting at £188. Both of these alternative options are worth considering when looking to reach your destination.

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

    Chicago and Boston Logan Intl are 847.9 mi apart from one another. Flights usually cover this in 2h 15m, depending on flying conditions and air traffic around both airports.

  • What is the carbon footprint of flying from Chicago to Boston Logan Intl?

    753lb is the expected carbon footprint of a flight from Chicago to Boston Logan Intl, though you can sort and filter momondo flight search results by CO2 to find the best option. By train, you could lower your emissions for this trip by about 75%. Emissions for travelling this route by bus are generally around 119lb.

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

    Prices for flights from Chicago to Boston Logan Intl Airport were last updated today.

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

    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 Chicago to Boston Logan Intl Airport.

  • What documentation or ID do you need to fly to Boston Logan Intl Airport?

    The travel and health documents you'll need for your trip to Boston Logan Intl Airport 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 Boston Logan Intl Airport. 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 Chicago to Boston?


Why use momondo?

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

Finding the right flight to Boston from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Boston quick and easy, saving you time and money.

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

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

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Boston.

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

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


Choose the best way to get from Chicago to Boston

Buses

25h 35m
£142 one-way£188 return
Direct · from £188

Distance to city centre

ZTO0.6 mi
119lb CO2

84% less than flights

Find Buses

Chicago to Boston Buses

Trains

21h 54m
£86 one-way£208 return
Direct · from £208

Distance to city centre

ZTO0.6 mi
ZTY1.3 mi
189lb CO2

75% less than flights

Find Trains

Chicago to Boston Trains

Flights

2h 15m
£59 one-way£84 return
Direct · from £1221 stop · from £131

Distance to city centre

BOS2.6 mi

An easier way to manage your Boston trip

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

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