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Cheap flights from Chicago to Boston from £34

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 7/8. 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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0 bags
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Cheap return flights

JetBlue Logo
09:42 - 13:10ORD-BOS
2h 28mdirect
JetBlue Logo
07:00 - 08:57BOS-ORD
2h 57mdirect
£67JetBlue
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Sat, 18 Oct - Sat, 25 Oct
JetBlue Logo
18:59 - 22:32ORD-BOS
2h 33mdirect
JetBlue Logo
16:05 - 17:55BOS-ORD
2h 50mdirect
£68JetBlue
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Thu, 4 Sep - Mon, 8 Sep
United Airlines Logo
15:48 - 19:18ORD-BOS
2h 30mdirect
United Airlines Logo
19:04 - 23:41BOS-ORD
5h 37m1 stop
£71United Airlines
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Wed, 6 Aug - Tue, 12 Aug
JetBlue Logo
18:50 - 22:23ORD-BOS
2h 33mdirect
JetBlue Logo
08:30 - 10:28BOS-ORD
2h 58mdirect
£72JetBlue
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Fri, 24 Oct - Mon, 27 Oct
Southwest Logo
13:30 - 22:15ORD-BOS
7h 45m1 stop
Southwest Logo
10:45 - 16:25BOS-ORD
6h 40m1 stop
£73Southwest
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Sat, 30 Aug - Thu, 4 Sep
Southwest Logo
15:10 - 22:30ORD-BOS
6h 20m1 stop
Southwest Logo
05:20 - 12:45BOS-ORD
8h 25m1 stop
£76Southwest
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Wed, 6 Aug - Tue, 12 Aug
Southwest Logo
15:10 - 22:30ORD-BOS
6h 20m1 stop
Southwest Logo
07:30 - 12:45BOS-ORD
6h 15m1 stop
£77Southwest
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Wed, 3 Sep - Mon, 8 Sep
United Airlines Logo
06:30 - 09:56ORD-BOS
2h 26mdirect
United Airlines Logo
06:10 - 08:05BOS-ORD
2h 55mdirect
£85United Airlines
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Sun, 31 Aug - Mon, 1 Sep
Delta Logo
07:00 - 10:30ORD-BOS
2h 30mdirect
Delta Logo
11:00 - 12:52BOS-ORD
2h 52mdirect
£86Delta
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Sat, 25 Oct - Sat, 1 Nov
Delta Logo
07:00 - 10:29ORD-BOS
2h 29mdirect
Delta Logo
06:00 - 10:05BOS-ORD
5h 05m1 stop
£93Delta
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Sat, 23 Aug - Tue, 26 Aug

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
6 Aug
ORD15:48Chicago O'Hare Intl
2h 30m
BOS19:18Boston Logan Intl
12 Aug
BOS19:04Boston Logan Intl
5h 37m
1 stop
ORD23:41Chicago O'Hare Intl
£71
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United Airlines
16 Jul
ORD20:05Chicago O'Hare Intl
2h 27m
BOS23:32Boston Logan Intl
18 Aug
BOS06:07Boston Logan Intl
2h 58m
ORD08:05Chicago O'Hare Intl
£84
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United Airlines
31 Aug
ORD06:30Chicago O'Hare Intl
2h 26m
BOS09:56Boston Logan Intl
1 Sept
BOS06:10Boston Logan Intl
2h 55m
ORD08:05Chicago O'Hare Intl
£85
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Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets
Southwest
30 Aug
ORD13:30Chicago O'Hare Intl
7h 45m
1 stop
BOS22:15Boston Logan Intl
4 Sept
BOS10:45Boston Logan Intl
6h 40m
1 stop
ORD16:25Chicago O'Hare Intl
£73
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Southwest
6 Aug
ORD15:10Chicago O'Hare Intl
6h 20m
1 stop
BOS22:30Boston Logan Intl
12 Aug
BOS05:20Boston Logan Intl
8h 25m
1 stop
ORD12:45Chicago O'Hare Intl
£76
Find similar
Southwest
3 Sept
ORD15:10Chicago O'Hare Intl
6h 20m
1 stop
BOS22:30Boston Logan Intl
8 Sept
BOS07:30Boston Logan Intl
6h 15m
1 stop
ORD12:45Chicago O'Hare Intl
£77
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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, August 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 £138. The month of September is another great option to travel to Boston, with average flight prices from Chicago averaging around £138.

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 Saturday when prices can be found for as low as £93. 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 Thursday because tickets tend to average around £580. 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 £146. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around £450 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?

You are more likely to see cheaper flights to Boston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around £169 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as £143 on momondo.

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

There are 4 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.

How have Chicago to Boston flight prices changed over time?

As of July 2025, prices for Chicago to Boston flights are approximately 49% 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

£34

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is £34. The best return flight deal from Chicago to Boston found on momondo in the last 72 hours is £67.
The fastest flight from Chicago to Boston takes 2h 24m
Direct flights go from Chicago to Boston every day.
There is 1 airport near Boston: Boston Logan Intl (BOS)
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  • 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 24m, depending on flying conditions and air traffic around both airports.

  • 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?

Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Salem
Cambridge
Burlington
Amherst
Randolph
Brookline
Braintree
Needham
Plymouth
Falmouth
York Beach
West Yarmouth
Somerville
Warwick
Concord
Cape Neddick
Hampton
Hull
South Portland
Revere

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.

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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