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Cheap flights from Chicago to Boston from £47

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 21/12. 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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0 bags
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JetBlue Logo
20:38 - 00:06ORD-BOS
2h 28mdirect
JetBlue Logo
15:35 - 17:44BOS-ORD
3h 09mdirect
£95JetBlue
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Fri, 12 Dec - Tue, 6 Jan
Southwest Logo
13:45 - 21:45ORD-BOS
7h 00m1 stop
Southwest Logo
05:10 - 12:15BOS-ORD
8h 05m1 stop
£97Southwest
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Fri, 9 Jan - Sat, 10 Jan
Delta Logo
17:59 - 01:27ORD-BOS
6h 28m1 stop
Delta Logo
19:52 - 21:47BOS-ORD
2h 55mdirect
£98Delta
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Fri, 12 Dec - Sun, 14 Dec
United Airlines Logo
13:55 - 17:13ORD-BOS
2h 18mdirect
United Airlines Logo
07:45 - 09:45BOS-ORD
3h 00mdirect
£99United Airlines
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Tue, 4 Nov - Thu, 6 Nov
United Airlines Logo
09:20 - 12:44ORD-BOS
2h 24mdirect
United Airlines Logo
07:45 - 09:45BOS-ORD
3h 00mdirect
£100United Airlines
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Thu, 30 Oct - Thu, 6 Nov
United Airlines Logo
06:15 - 09:30ORD-BOS
2h 15mdirect
United Airlines Logo
15:10 - 17:10BOS-ORD
3h 00mdirect
£101United Airlines
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Thu, 30 Oct - Thu, 30 Oct
Southwest Logo
13:45 - 21:45ORD-BOS
7h 00m1 stop
Southwest Logo
05:00 - 12:15BOS-ORD
8h 15m1 stop
£101Southwest
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Fri, 9 Jan - Thu, 15 Jan
Delta Logo
07:05 - 10:29ORD-BOS
2h 24mdirect
Delta Logo
12:45 - 14:47BOS-ORD
3h 02mdirect
£102Delta
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Mon, 3 Nov - Thu, 13 Nov
Delta Logo
11:15 - 19:33ORD-BOS
7h 18m1 stop
Delta Logo
18:25 - 00:01BOS-ORD
6h 36m1 stop
£105Delta
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Wed, 3 Dec - Fri, 5 Dec
Delta Logo
07:10 - 10:35ORD-BOS
2h 25mdirect
Delta Logo
19:52 - 21:47BOS-ORD
2h 55mdirect
£106Delta
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Wed, 19 Nov - Tue, 2 Dec

Delta flights from Chicago to Boston

Our best Delta deals on Chicago to Boston flight tickets
Delta
12 Dec
ORD17:59Chicago O'Hare Intl
6h 28m
1 stop
BOS01:27Boston Logan Intl
14 Dec
BOS19:52Boston Logan Intl
2h 55m
ORD21:47Chicago O'Hare Intl
£98
Find similar
Delta
3 Nov
ORD07:05Chicago O'Hare Intl
2h 24m
BOS10:29Boston Logan Intl
13 Nov
BOS12:45Boston Logan Intl
3h 02m
ORD14:47Chicago O'Hare Intl
£102
Find similar
Delta
3 Dec
ORD11:15Chicago O'Hare Intl
7h 18m
1 stop
BOS19:33Boston Logan Intl
5 Dec
BOS18:25Boston Logan Intl
6h 36m
1 stop
ORD00:01Chicago O'Hare Intl
£105
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United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
4 Nov
ORD13:55Chicago O'Hare Intl
2h 18m
BOS17:13Boston Logan Intl
6 Nov
BOS07:45Boston Logan Intl
3h 00m
ORD09:45Chicago O'Hare Intl
£99
Find similar
United Airlines
30 Oct
ORD09:20Chicago O'Hare Intl
2h 24m
BOS12:44Boston Logan Intl
6 Nov
BOS07:45Boston Logan Intl
3h 00m
ORD09:45Chicago O'Hare Intl
£100
Find similar
United Airlines
30 Oct
ORD06:15Chicago O'Hare Intl
2h 15m
BOS09:30Boston Logan Intl
30 Oct
BOS15:10Boston Logan Intl
3h 00m
ORD17:10Chicago O'Hare Intl
£101
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momondo Fare Finder

 
Customise your flight search to find flights from Chicago to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 279,928 searches. Data last updated 21 October 2025.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/12

20:38-00:06

Nonstop2h 28m

Boston Logan Intl

Tue 6/1

15:35-17:44

Nonstop3h 09m

£95

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/1

13:45-21:45

1 stop7h 00m

Boston Logan Intl

Sat 10/1

05:10-12:15

1 stop8h 05m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/12

17:59-01:27

1 stop6h 28m

Boston Logan Intl

Sun 14/12

19:52-21:47

Nonstop2h 55m

£98

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/11

13:55-17:13

Nonstop2h 18m

Boston Logan Intl

Thu 6/11

07:45-09:45

Nonstop3h 00m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 30/10

09:20-12:44

Nonstop2h 24m

Boston Logan Intl

Thu 6/11

07:45-09:45

Nonstop3h 00m

£100

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 30/10

06:15-09:30

Nonstop2h 15m

Boston Logan Intl

Thu 30/10

15:10-17:10

Nonstop3h 00m

£101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/1

13:45-21:45

1 stop7h 00m

Boston Logan Intl

Thu 15/1

05:00-12:15

1 stop8h 15m

£101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/11

07:05-10:29

Nonstop2h 24m

Boston Logan Intl

Thu 13/11

12:45-14:47

Nonstop3h 02m

£102

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/12

11:15-19:33

1 stop7h 18m

Boston Logan Intl

Fri 5/12

18:25-00:01

1 stop6h 36m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 19/11

07:10-10:35

Nonstop2h 25m

Boston Logan Intl

Tue 2/12

19:52-21:47

Nonstop2h 55m

£106

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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, 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 £154. The month of January is another great option to travel to Boston, with average flight prices from Chicago averaging around £162.

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 Monday when prices can be found for as low as £210. 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 Wednesday because tickets tend to average around £562. 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 in the morning. Flights from Chicago to Boston during this time can be as low as £380. At midday is when there is more demand to fly to Boston, so prices are often more expensive at around £570 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 £176 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 £140 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 October 2025, prices for Chicago to Boston flights are approximately 5% 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

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Boston

1 airport
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)
Search flight deals

  • 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.

  • 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
Waltham
Cambridge
Amherst
Burlington
Falmouth
Plymouth
Braintree
Randolph
Needham
Revere
York Beach
West Yarmouth
Somerville
Warwick
Concord
Hampton
Hull
Cape Neddick
South Portland

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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