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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 9/15. 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 round-trip flights

Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:50 am - 7:25 amBOS-MDW
2h 35mnonstop
$67Southwest
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Sat, Sep 6 - Sat, Sep 13
Southwest Logo
1:30 pm - 4:45 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$72Southwest
Find Deal
Wed, Dec 10 - Tue, Dec 16
JetBlue Logo
11:30 am - 2:46 pmORD-BOS
2h 16mnonstop
JetBlue Logo
4:55 pm - 7:05 pmBOS-ORD
3h 10mnonstop
$88JetBlue
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Tue, Nov 4 - Tue, Nov 4
JetBlue Logo
9:50 am - 1:16 pmORD-BOS
2h 26mnonstop
JetBlue Logo
7:10 am - 9:04 amBOS-ORD
2h 54mnonstop
$90JetBlue
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Sat, Jan 24 - Mon, Jan 26
American Airlines Logo
5:36 pm - 9:00 pmORD-BOS
2h 24mnonstop
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
$92American Airlines
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Sat, Sep 6 - Mon, Sep 8
American Airlines Logo
8:25 pm - 11:53 pmORD-BOS
2h 28mnonstop
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
$94American Airlines
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Thu, Sep 4 - Mon, Sep 8
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
8:27 pm - 10:15 pmBOS-ORD
2h 48mnonstop
$99United Airlines
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Fri, Sep 19 - Sun, Sep 21
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
$111United Airlines
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Fri, Sep 5 - Mon, Sep 15
Delta Logo
6:00 pm - 9:38 pmORD-BOS
2h 38mnonstop
Delta Logo
7:55 pm - 9:56 pmBOS-ORD
3h 01mnonstop
$117Delta
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Wed, Sep 3 - Tue, Sep 9
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
Delta Logo
11:00 am - 4:26 pmBOS-ORD
6h 26m1 stop
$137Delta
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Tue, Aug 19 - Tue, Aug 26

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets
JetBlue
Nov 4
ORD11:30 amChicago O'Hare Intl
2h 16m
BOS2:46 pmBoston Logan Intl
Nov 4
BOS4:55 pmBoston Logan Intl
3h 10m
ORD7:05 pmChicago O'Hare Intl
$88
Find similar
JetBlue
Jan 24
ORD9:50 amChicago O'Hare Intl
2h 26m
BOS1:16 pmBoston Logan Intl
Jan 26
BOS7:10 amBoston Logan Intl
2h 54m
ORD9:04 amChicago O'Hare Intl
$90
Find similar
JetBlue
Sep 4
ORD6:59 pmChicago O'Hare Intl
2h 33m
BOS10:32 pmBoston Logan Intl
Sep 11
BOS7:00 amBoston Logan Intl
2h 56m
ORD8:56 amChicago O'Hare Intl
$91
Find similar

Delta flights from Chicago to Boston

Our best Delta deals on Chicago to Boston flight tickets
Delta
Sep 3
ORD6:00 pmChicago O'Hare Intl
2h 38m
BOS9:38 pmBoston Logan Intl
Sep 9
BOS7:55 pmBoston Logan Intl
3h 01m
ORD9:56 pmChicago O'Hare Intl
$117
Find similar
Delta
Aug 19
ORD7:00 amChicago O'Hare Intl
2h 29m
BOS10:29 amBoston Logan Intl
Aug 27
BOS7:20 amBoston Logan Intl
2h 56m
ORD9:16 amChicago O'Hare Intl
$127
Find similar
Delta
Aug 19
ORD7:00 amChicago O'Hare Intl
2h 29m
BOS10:29 amBoston Logan Intl
Aug 26
BOS11:00 amBoston Logan Intl
6h 26m
1 stop
ORD4:26 pmChicago O'Hare Intl
$137
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momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated August 5, 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

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/6

5:40 pm-9:00 pm

Nonstop2h 20m

Boston Logan Intl

Sat 9/13

5:50 am-7:25 am

Nonstop2h 35m

$67

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/10

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Tue 12/16

5:35 pm-9:05 pm

1 stop4h 30m

$72

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/4

11:30 am-2:46 pm

Nonstop2h 16m

Boston Logan Intl

Tue 11/4

4:55 pm-7:05 pm

Nonstop3h 10m

$88

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/24

9:50 am-1:16 pm

Nonstop2h 26m

Boston Logan Intl

Mon 1/26

7:10 am-9:04 am

Nonstop2h 54m

$90

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/6

5:36 pm-9:00 pm

Nonstop2h 24m

Boston Logan Intl

Mon 9/8

5:00 am-6:51 am

Nonstop2h 51m

$92

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

Mon 9/8

5:00 am-6:51 am

Nonstop2h 51m

$94

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/19

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Sun 9/21

8:27 pm-10:15 pm

Nonstop2h 48m

$99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/5

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Mon 9/15

6:10 am-8:05 am

Nonstop2h 55m

$111

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/3

6:00 pm-9:38 pm

Nonstop2h 38m

Boston Logan Intl

Tue 9/9

7:55 pm-9:56 pm

Nonstop3h 01m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/19

7:00 am-10:29 am

Nonstop2h 29m

Boston Logan Intl

Tue 8/26

11:00 am-4:26 pm

1 stop6h 26m

$137

Flights are sorted by cheapest round-trip 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 $189. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago during August instead. Flights to Boston in August, while not as cheap as those in September, still average around $206.

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

The cheapest day to depart from Chicago to Boston is on a Thursday when prices can be found for as low as $239. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $301.

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

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago to Boston in the evening for as low as $217. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $280 per ticket.

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

Fly from Chicago Midway 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 $229 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as $182 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 August 2025, prices for Chicago to Boston flights are approximately 42% 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 round-trip 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 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 $34. The best round-trip 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 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?

    The distance between Chicago and Boston Logan Intl is about 847.9 mi. 2h 15m is a normal flight duration for this route.

  • 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 are updated daily.

  • How many operators does momondo search for flights from Chicago to Boston Logan Intl Airport?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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?

  • What is the most popular airline from Chicago to Boston?

Best airlines flying from Chicago to Boston

Compare and see reviews for airlines that fly from Chicago to Boston with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $35Free CancellationRating
6.3
8,054 reviews
Search Spirit Airlines flights
JetBluePriceFrom $78Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $90Free CancellationRating
8.0
7,987 reviews
Search Delta flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
American AirlinesPriceFrom $122Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $131Free CancellationRating
7.4
8,915 reviews
Search United Airlines flights
SouthwestPriceFrom $153Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Delta Flights From Chicago to Boston

    Delta flight deals from Chicago to Boston start from $90 round-trip. Over the 11 Delta flights for this route in a normal week, average airfare is usually $220 round-trip - but some users have found much cheaper deals with momondo.

  • Southwest Flights From Chicago to Boston

    Another popular option for Chicago to Boston flights is Southwest (8.0/10, 4,246 ratings). Southwest flies from Chicago to Boston around 6 times per week, with deals starting from $153 round-trip and rising to an average price of around $263.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Salem
Ogunquit
Hampton
Old Orchard Beach
York Beach
Plymouth
Kennebunkport
Nashua
Cambridge
Narragansett
Laconia
Brockton
South Yarmouth
Gloucester
Concord
Everett
Wells
Falmouth
Sturbridge

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Boston. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Boston on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Boston from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Boston flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Boston trip

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