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Cheap flights from Chicago to Boston from $64

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 2/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:00 am - 5:15 pm
ORD
-
BOS
9h 15m
1 stop
Multiple Airlines Logo
6:00 am - 10:51 am
BOS
-
ORD
29h 51m
1 stop
$131Multiple Airlines
火, 2月 17 - 金, 2月 27
Multiple Airlines Logo
6:02 pm - 1:13 am
ORD
-
BOS
6h 11m
1 stop
Multiple Airlines Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
$132Multiple Airlines
水, 2月 25 - 土, 2月 28
Southwest Logo
6:10 pm - 9:25 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
2:10 pm - 7:25 pm
BOS
-
MDW
6h 15m
1 stop
$133Southwest
土, 2月 14 - 土, 2月 21
JetBlue Logo
7:40 am - 11:05 am
ORD
-
BOS
2h 25mnonstop
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
$133JetBlue
金, 2月 6 - 月, 2月 9
Southwest Logo
6:35 pm - 9:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
$135Southwest
金, 2月 6 - 日, 2月 8
JetBlue Logo
7:40 am - 11:05 am
ORD
-
BOS
2h 25mnonstop
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
$135JetBlue
金, 2月 6 - 日, 2月 8
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
Delta Logo
7:15 am - 9:28 am
BOS
-
ORD
3h 13mnonstop
$136Delta
日, 2月 15 - 水, 3月 4
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
Delta Logo
7:15 am - 9:28 am
BOS
-
ORD
3h 13mnonstop
$137Delta
木, 2月 19 - 日, 2月 22
Spirit Airlines Logo
10:44 am - 10:01 pm
ORD
-
BOS
10h 17m
1 stop
Spirit Airlines Logo
5:40 am - 6:21 pm
BOS
-
ORD
13h 41m
1 stop
$140Spirit Airlines
火, 3月 10 - 水, 3月 18
Spirit Airlines Logo
10:44 am - 10:01 pm
ORD
-
BOS
10h 17m
1 stop
Spirit Airlines Logo
5:40 am - 6:21 pm
BOS
-
ORD
13h 41m
1 stop
$141Spirit Airlines
水, 3月 11 - 水, 3月 18

Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets
Southwest
Feb 14
MDW6:10 pmChicago Midway
2h 15m
BOS9:25 pmBoston Logan Intl
Feb 21
BOS2:10 pmBoston Logan Intl
6h 15m
1 stop
MDW7:25 pmChicago Midway
$133
Southwest
Feb 6
MDW6:35 pmChicago Midway
2h 15m
BOS9:50 pmBoston Logan Intl
Feb 8
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
$135
Southwest
Feb 7
MDW10:15 amChicago Midway
2h 15m
BOS1:30 pmBoston Logan Intl
Feb 9
BOS5:20 amBoston Logan Intl
2h 50m
MDW7:10 amChicago Midway
$136

Spirit Airlines flights from Chicago to Boston

Our best Spirit Airlines deals on Chicago to Boston flight tickets
Spirit Airlines
Mar 10
ORD10:44 amChicago O'Hare Intl
10h 17m
1 stop
BOS10:01 pmBoston Logan Intl
Mar 18
BOS5:40 amBoston Logan Intl
13h 41m
1 stop
ORD6:21 pmChicago O'Hare Intl
$140
Spirit Airlines
Mar 11
ORD10:44 amChicago O'Hare Intl
10h 17m
1 stop
BOS10:01 pmBoston Logan Intl
Mar 18
BOS5:40 amBoston Logan Intl
13h 41m
1 stop
ORD6:21 pmChicago O'Hare Intl
$141
Spirit Airlines
Mar 11
ORD5:15 amChicago O'Hare Intl
11h 00m
1 stop
BOS5:15 pmBoston Logan Intl
Mar 18
BOS5:40 amBoston Logan Intl
13h 41m
1 stop
ORD6:21 pmChicago O'Hare Intl
$143

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 1月 27, 2026.
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

火 2/17

7:00 am-5:15 pm

1 stop9h 15m

Boston Logan Intl

金 2/27

6:00 am-10:51 am

1 stop29h 51m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

水 2/25

6:02 pm-1:13 am

1 stop6h 11m

Boston Logan Intl

土 2/28

7:00 am-9:10 am

Nonstop3h 10m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

土 2/14

6:10 pm-9:25 pm

Nonstop2h 15m

Boston Logan Intl

土 2/21

2:10 pm-7:25 pm

1 stop6h 15m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

金 2/6

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

月 2/9

3:35 pm-5:43 pm

Nonstop3h 08m

$133

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

金 2/6

6:35 pm-9:50 pm

Nonstop2h 15m

Boston Logan Intl

日 2/8

5:30 am-7:20 am

Nonstop2h 50m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

金 2/6

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

日 2/8

3:35 pm-5:43 pm

Nonstop3h 08m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

日 2/15

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

水 3/4

7:15 am-9:28 am

Nonstop3h 13m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

木 2/19

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

日 2/22

7:15 am-9:28 am

Nonstop3h 13m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

火 3/10

10:44 am-10:01 pm

1 stop10h 17m

Boston Logan Intl

水 3/18

5:40 am-6:21 pm

1 stop13h 41m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

水 3/11

10:44 am-10:01 pm

1 stop10h 17m

Boston Logan Intl

水 3/18

5:40 am-6:21 pm

1 stop13h 41m

$141

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 cheapest month to fly to Boston?

In general, January 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 $207. If you aren’t able to travel during the month of January, then book flights to Boston from Chicago during September instead. Flights to Boston in September, while not as cheap as those in January, still average around $207.

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

The cheapest day to depart from Chicago to Boston is on a Wednesday when prices can be found for as low as $238. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $298.

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 $214. 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 $293 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 $228 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 $188 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 January 2026, 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 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

$78

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Boston

1 airport
The best one-way flight to Boston from Chicago in the past 72 hours is $78. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $165.
The fastest flight from Chicago to Boston takes 2h 10m
Direct flights go from Chicago to Boston every day.
There is 1 airport in Boston. From Chicago there are direct flights to 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 10m 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
JetBluePriceFrom $61Free CancellationRating
7.2
2,889 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $79Free CancellationRating
6.3
8,382 reviews
Search Spirit Airlines flights
DeltaPriceFrom $94Free CancellationRating
7.9
8,117 reviews
Search Delta flights
American AirlinesPriceFrom $117Free CancellationRating
7.2
11,195 reviews
Search American Airlines flights
United AirlinesPriceFrom $117Free CancellationRating
7.4
9,203 reviews
Search United Airlines flights
SouthwestPriceFrom $136Free CancellationRating
8.0
4,268 reviews
Search Southwest flights

  • Southwest Flights From Chicago to Boston

    Southwest flight deals from Chicago to Boston start from $136 round-trip. Over the 10 Southwest flights for this route in a normal week, average airfare is usually $245 round-trip - but some users have found much cheaper deals with momondo.

  • Delta Flights From Chicago to Boston

    Another popular option for Chicago to Boston flights is Delta (7.9/10, 8,118 ratings). Delta flies from Chicago to Boston around 17 times per week, with deals starting from $94 round-trip and rising to an average price of around $217.

Traveling to a place near Boston?

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

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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