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Cheap flights from Chicago to Boston 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 Chicago to Boston departing on 14/1. 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 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.
15:00 - 00:30ORD-BOS
8h 30m1 stop
06:00 - 11:47BOS-ORD
6h 47m1 stop
£79Frontier
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Tue, 14 Jan - Wed, 15 Jan
09:05 - 12:23ORD-BOS
2h 18mdirect
08:10 - 10:12BOS-ORD
3h 02mdirect
£124JetBlue
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Thu, 9 Jan - Tue, 14 Jan
17:05 - 22:58ORD-BOS
4h 53m1 stop
15:52 - 17:55BOS-ORD
3h 03mdirect
£131JetBlue
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Fri, 7 Feb - Tue, 11 Feb
07:10 - 10:47ORD-BOS
2h 37mdirect
15:30 - 17:36BOS-ORD
3h 06mdirect
£147Delta
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Mon, 20 Jan - Wed, 22 Jan
11:53 - 17:27ORD-BOS
4h 34m1 stop
07:10 - 11:40BOS-ORD
5h 30m1 stop
£155United Airlines
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Wed, 5 Mar - Sun, 9 Mar
07:20 - 15:09ORD-BOS
6h 49m1 stop
09:20 - 11:22BOS-ORD
3h 02mdirect
£156United Airlines
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Fri, 14 Feb - Mon, 17 Mar
07:35 - 11:03ORD-BOS
2h 28mdirect
07:15 - 09:25BOS-ORD
3h 10mdirect
£157Delta
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Fri, 3 Jan - Mon, 6 Jan
13:50 - 17:32ORD-BOS
2h 42mdirect
11:00 - 12:53BOS-ORD
2h 53mdirect
£158Delta
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Tue, 10 Jun - Wed, 18 Jun
08:34 - 00:13ORD-BOS
14h 39m2 stops
12:15 - 23:32BOS-ORD
12h 17m2 stops
£162Spirit Airlines
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Tue, 14 Jan - Wed, 15 Jan
07:00 - 00:13ORD-BOS
16h 13m3 stops
12:15 - 23:32BOS-ORD
12h 17m2 stops
£185Spirit Airlines
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Tue, 14 Jan - Wed, 15 Jan
07:00 - 10:15ORD-BOS
2h 15mdirect
£62JetBlue
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Tue, 14 Jan
16:15 - 19:38ORD-BOS
2h 23mdirect
£62United Airlines
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Mon, 13 Jan
17:05 - 00:18ORD-BOS
6h 13m1 stop
£69JetBlue
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Fri, 17 Jan
14:35 - 18:06ORD-BOS
2h 31mdirect
£70Delta
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Tue, 18 Feb
07:35 - 11:03ORD-BOS
2h 28mdirect
£75Delta
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Wed, 25 Dec
11:25 - 22:30ORD-BOS
10h 05m2 stops
£121Southwest
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Mon, 3 Feb
13:30 - 07:45ORD-BOS
17h 15m2 stops
£130Southwest
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Sat, 1 Mar
15:35 - 16:55ORD-BOS
24h 20m2 stops
£158Alaska Airlines
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Fri, 24 Jan
18:55 - 23:59ORD-BOS
28h 04m2 stops
£159Alaska Airlines
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Wed, 22 Jan
19:13 - 10:35ORD-BOS
14h 22m1 stop
£160Sun Country Air
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Thu, 24 Apr
18:25 - 21:54ORD-BOS
2h 29mdirect
12:12 - 14:10BOS-ORD
2h 58mdirect
£218United Airlines
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Thu, 19 Dec - Thu, 16 Jan
07:46 - 11:12ORD-BOS
2h 26mdirect
19:42 - 23:25BOS-ORD
4h 43m1 stop
£219United Airlines
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Mon, 23 Dec - Tue, 31 Dec
07:46 - 11:12ORD-BOS
2h 26mdirect
06:02 - 08:05BOS-ORD
3h 03mdirect
£225United Airlines
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Mon, 23 Dec - Tue, 31 Dec
13:59 - 22:40ORD-BOS
7h 41m1 stop
09:00 - 11:03BOS-ORD
3h 03mdirect
£242Delta
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Fri, 20 Dec - Wed, 25 Dec
10:11 - 15:59ORD-BOS
4h 48m1 stop
06:00 - 08:07BOS-ORD
3h 07mdirect
£261JetBlue
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Mon, 23 Dec - Fri, 3 Jan
08:42 - 12:11ORD-BOS
2h 29mdirect
06:00 - 08:07BOS-ORD
3h 07mdirect
£278JetBlue
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Mon, 23 Dec - Fri, 3 Jan
14:55 - 00:05ORD-BOS
8h 10m2 stops
08:20 - 12:45BOS-ORD
5h 25m1 stop
£281Southwest
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Mon, 23 Dec - Sat, 11 Jan
14:55 - 00:20ORD-BOS
8h 25m2 stops
06:15 - 15:20BOS-ORD
10h 05m2 stops
£285Southwest
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Mon, 23 Dec - Sat, 11 Jan
07:35 - 11:03ORD-BOS
2h 28mdirect
19:40 - 21:41BOS-ORD
3h 01mdirect
£293Delta
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Mon, 23 Dec - Mon, 30 Dec
07:00 - 19:20ORD-BOS
11h 20m1 stop
16:30 - 16:27BOS-ORD
24h 57m2 stops
£788Alaska Airlines
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Thu, 19 Dec - Thu, 16 Jan
09:05 - 12:23ORD-BOS
2h 18mdirect
08:10 - 10:12BOS-ORD
3h 02mdirect
£124JetBlue
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Thu, 9 Jan - Tue, 14 Jan
07:00 - 10:15ORD-BOS
2h 15mdirect
06:10 - 08:14BOS-ORD
3h 04mdirect
£132JetBlue
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Fri, 17 Jan - Fri, 24 Jan
13:00 - 16:20ORD-BOS
2h 20mdirect
13:41 - 15:40BOS-ORD
2h 59mdirect
£140JetBlue
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Thu, 27 Feb - Sat, 1 Mar
08:42 - 12:12ORD-BOS
2h 30mdirect
06:10 - 08:14BOS-ORD
3h 04mdirect
£140JetBlue
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Mon, 6 Jan - Fri, 10 Jan
07:10 - 10:47ORD-BOS
2h 37mdirect
07:15 - 09:25BOS-ORD
3h 10mdirect
£147Delta
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Mon, 20 Jan - Sat, 25 Jan
07:35 - 11:03ORD-BOS
2h 28mdirect
07:15 - 09:25BOS-ORD
3h 10mdirect
£157Delta
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Fri, 3 Jan - Mon, 6 Jan
06:30 - 09:58ORD-BOS
2h 28mdirect
11:00 - 12:53BOS-ORD
2h 53mdirect
£158Delta
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Tue, 10 Jun - Tue, 17 Jun
21:30 - 00:54ORD-BOS
2h 24mdirect
11:05 - 13:03BOS-ORD
2h 58mdirect
£176United Airlines
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Thu, 2 Jan - Mon, 6 Jan
21:30 - 00:54ORD-BOS
2h 24mdirect
06:02 - 08:00BOS-ORD
2h 58mdirect
£193United Airlines
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Sat, 4 Jan - Sun, 5 Jan
21:30 - 00:50ORD-BOS
2h 20mdirect
06:00 - 08:04BOS-ORD
3h 04mdirect
£203United Airlines
Find Deal
Thu, 27 Mar - Fri, 28 Mar

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets
JetBlue
9 Jan
ORD09:05Chicago O'Hare Intl
2h 18m
BOS12:23Boston Logan Intl
14 Jan
BOS08:10Boston Logan Intl
3h 02m
ORD10:12Chicago O'Hare Intl
JetBlue
7 Feb
ORD17:05Chicago O'Hare Intl
4h 53m
1 stop
BOS22:58Boston Logan Intl
11 Feb
BOS15:52Boston Logan Intl
3h 03m
ORD17:55Chicago O'Hare Intl
JetBlue
9 Jan
ORD07:00Chicago O'Hare Intl
2h 15m
BOS10:15Boston Logan Intl
13 Jan
BOS08:35Boston Logan Intl
8h 09m
1 stop
ORD15:44Chicago O'Hare Intl

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
5 Mar
ORD11:53Chicago O'Hare Intl
4h 34m
1 stop
BOS17:27Boston Logan Intl
9 Mar
BOS07:10Boston Logan Intl
5h 30m
1 stop
ORD11:40Chicago O'Hare Intl
United Airlines
14 Feb
ORD07:20Chicago O'Hare Intl
6h 49m
1 stop
BOS15:09Boston Logan Intl
17 Mar
BOS09:20Boston Logan Intl
3h 02m
ORD11:22Chicago O'Hare Intl
United Airlines
2 Jan
ORD21:30Chicago O'Hare Intl
2h 24m
BOS00:54Boston Logan Intl
8 Jan
BOS10:57Boston Logan Intl
2h 58m
ORD12:55Chicago 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 typical price of a round-trip flight between Chicago and Boston?

What is the cheapest month to fly to Boston?

In general, September is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around £151. The month of January is another great option to travel to Boston, with average flight prices from Chicago averaging around £155.

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

The cheapest day to depart on your flight to Boston is on a Thursday 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. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around £280. These prices are subject to change though, so be sure to set up a Price Alert for flights to Boston.

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

Our most recent data shows that the best time of day to fly to Boston is at midday. Flights from Chicago to Boston during this time can be as low as £0. In the morning is when there is more demand to fly to Boston, so prices are often more expensive at around £187 per ticket.

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

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

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

The best time to book a flight to Boston from Chicago is 58 days out, which is when prices tend to be around £191. Don’t hesitate to check prices now though, because momondo users recently found tickets for as low as £110.

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

There are 3 cabin classes available to choose from on Chicago to Boston Logan Intl 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 Chicago to Boston flights?

You could potentially save up to 12% 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 December 2024, prices for Chicago to Boston flights are approximately 3% more expensive 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

£62

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 £62. The best return flight deal from Chicago to Boston found on momondo in the last 72 hours is £79.
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 £186, or consider a bus from Chicago to Boston starting at £193. 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
£87 one-way£193 return
Direct · from £193

Distance to city centre

ZTO0.6 mi
119lb CO2

84% less than flights

Find Buses

Chicago to Boston Buses

Trains

21h 54m
£85 one-way£186 return
Direct · from £186

Distance to city centre

ZTO0.6 mi
189lb CO2

75% less than flights

Find Trains

Chicago to Boston Trains

Flights

2h 15m
£62 one-way£79 return
Direct · from £1241 stop · from £131

Distance to city centre

BOS2.6 mi

An easier way to manage your Boston trip

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