Cheap flights from Chicago to Boston from $69

Round-trip
1 adult
Economy
0 bags
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Sun 10/9
Sun 10/16

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Flight information for Chicago to Boston
(CHI to BOS)

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston

Best Price Found

$69

Fastest flight time

2h 16m

Direct flights

Wed, Thu, Sat and Sun

Airports in Boston

2 airports
The best one-way flight to Boston from Chicago in the past 72 hours is $69. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $138.
The fastest flight from Chicago to Boston takes 2h 16m
Direct flights go from Chicago to Boston on Wednesday, Thursday, Saturday and Sunday. The only airline offering direct flights is American Airlines.
There are 2 airports near Boston: Boston Logan Intl (BOS), Boston Harbor SPB (BNH)

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 from Chicago to Boston?

January. The cheapest time of year to fly to Boston from Chicago is January. Most expensive is June

What is the cheapest day to depart Chicago for Boston?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Chicago to Boston?

in the evening. Chicago to Boston flights are approximately 14% more expensive at noon than in the evening

What is the cheapest airline that flies to Boston from Chicago?

Juneyao Airlines. American Airlines, JetBlue, and Juneyao Airlines are the most popular carriers operating from Chicago to Boston

What is the cheapest Chicago to Boston flight route?

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

How far in advance should you book Chicago to Boston flights?

0 days before. The cheapest time to buy a flight from Chicago to Boston is approximately 0 days to departure

When traveling from Chicago to Boston, the most popular airport to fly into is Boston Logan Intl Airport. The majority of travelers flying into Boston Logan Intl Airport from Chicago are departing from Chicago O'Hare Intl Airport. When booking your trip to Boston, it is helpful to have an alternative airport to fly out of. The nearest airport to Chicago O'Hare Intl Airport is Chicago Midway Airport which is located in Chicago. When traveling from Chicago, it is helpful to have an alternative airport to fly into when you land in Boston. The nearest airport to Boston Logan Intl Airport is Worcester Airport which is located in Worcester. In October, $138 is typically the cheapest round trip price you’ll find from Chicago to Boston which you can find when you fly ORD — BOS.

Chicago O'Hare Intl Airport (ORD) to Boston Logan Intl Airport (BOS)$138
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Chicago Midway Airport (MDW) to Boston Logan Intl Airport (BOS)$164
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Chicago O'Hare Intl Airport (ORD) to Worcester Airport (ORH)$165
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Easily compare round-trip flights from Chicago to Boston

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Boston by changing tabs
United Airlines
Oct 26
ORD2:00 amChicago O'Hare Intl
2h 22m
BOS4:22 amBoston Logan Intl
Oct 26
BOS9:07 amBoston Logan Intl
2h 48m
ORD11:55 amChicago O'Hare Intl
Multiple Airlines
Oct 18
ORD3:45 amChicago O'Hare Intl
2h 20m
BOS6:05 amBoston Logan Intl
Oct 21
BOS6:05 amBoston Logan Intl
8h 59m
1 stop
ORD3:04 pmChicago O'Hare Intl
JetBlue
Oct 15
ORD2:45 pmChicago O'Hare Intl
2h 24m
BOS5:09 pmBoston Logan Intl
Oct 19
BOS7:15 amBoston Logan Intl
5h 04m
1 stop
ORD12:19 pmChicago O'Hare Intl
Southwest
Oct 17
MDW1:45 amChicago Midway
2h 10m
BOS3:55 amBoston Logan Intl
Oct 20
BOS5:40 pmBoston Logan Intl
2h 40m
MDW8:20 pmChicago Midway
Frontier
Nov 3
MDW1:32 pmChicago Midway
14h 04m
1 stop
BOS3:36 amBoston Logan Intl
Nov 7
BOS4:11 amBoston Logan Intl
16h 45m
1 stop
MDW8:56 pmChicago Midway
American Airlines
Oct 18
ORD3:38 amChicago O'Hare Intl
4h 52m
1 stop
BOS8:30 amBoston Logan Intl
Oct 18
BOS11:30 amBoston Logan Intl
5h 10m
1 stop
ORD4:40 pmChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Boston

If you're looking for one-way flights from Chicago to Boston, view some of our deals below provided by American Airlines, Frontier and JetBlue
JetBlue
Nov 2
ORD3:00 pmChicago O'Hare Intl
2h 18m
BOS5:18 pmBoston Logan Intl
United Airlines
Oct 24
ORD5:37 pmChicago O'Hare Intl
2h 23m
BOS8:00 pmBoston Logan Intl
Frontier
Oct 25
MDW12:26 pmChicago Midway
13h 39m
1 stop
BOS2:05 amBoston Logan Intl

Search last-minute flights to Boston from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Boston
United Airlines
Oct 14
ORD5:37 pmChicago O'Hare Intl
2h 23m
BOS8:00 pmBoston Logan Intl
Oct 18
BOS3:30 amBoston Logan Intl
2h 51m
ORD6:21 amChicago O'Hare Intl
JetBlue
Oct 14
ORD2:45 pmChicago O'Hare Intl
2h 24m
BOS5:09 pmBoston Logan Intl
Oct 19
BOS7:15 amBoston Logan Intl
5h 04m
1 stop
ORD12:19 pmChicago O'Hare Intl
American Airlines
Oct 12
ORD2:15 amChicago O'Hare Intl
2h 15m
BOS4:30 amBoston Logan Intl
Oct 19
BOS2:15 amBoston Logan Intl
3h 04m
ORD5:19 amChicago O'Hare Intl
Multiple Airlines
Oct 12
ORD2:15 amChicago O'Hare Intl
2h 26m
BOS4:41 amBoston Logan Intl
Oct 19
BOS11:55 amBoston Logan Intl
3h 02m
ORD2:57 pmChicago O'Hare Intl
Delta
Oct 11
MDW9:49 amChicago Midway
5h 31m
1 stop
BOS3:20 pmBoston Logan Intl
Oct 12
BOS1:40 amBoston Logan Intl
4h 02m
1 stop
MDW5:42 amChicago Midway
Frontier
Oct 14
MDW10:51 amChicago Midway
16h 45m
2 stops
BOS3:36 amBoston Logan Intl
Oct 18
BOS5:41 amBoston Logan Intl
8h 24m
1 stop
MDW2:05 pmChicago Midway

Best airlines flying from Chicago to Boston

Compare and see reviews for airlines that fly from Chicago to Boston with momondo
AirlineRatingFree CancellationPrice
Juneyao AirlinesPriceFrom $14Free CancellationRating
0.0
Search Juneyao Airlines flights
JetBluePriceFrom $58Free CancellationRating
7.0
7.1

Boarding

7.4

Comfort

7.7

Crew

7.1

Entertainment

6.5

Food

Reviews

tvs, nothing else all good.

1 / 10
Search JetBlue flights
Spirit AirlinesPriceFrom $68Free CancellationRating
6.3
6.5

Boarding

5.9

Comfort

7.0

Crew

4.9

Entertainment

5.1

Food

Reviews

The flight got canceled 3hrs before take off. Next flight was over a 12hr wait. Had to take a different airline. Didn't get a full refund back after either. Never again will I fly Spirit.

1 / 10
Search Spirit Airlines flights
DeltaPriceFrom $82Free CancellationRating
7.9
7.9

Boarding

8.0

Comfort

8.3

Crew

7.8

Entertainment

7.3

Food

Reviews

One of the crew member weren’t to pleasant

1 / 10
Search Delta flights
United AirlinesPriceFrom $83Free CancellationRating
7.2
7.5

Boarding

7.1

Comfort

8.0

Crew

6.9

Entertainment

6.5

Food

Reviews

very bad food

1 / 10
Search United Airlines flights
American AirlinesPriceFrom $101Free CancellationRating
7.1
7.4

Boarding

7.2

Comfort

7.9

Crew

6.9

Entertainment

6.4

Food

Reviews

They canceled my flight

1 / 10
Search American Airlines flights
Alaska AirlinesPriceFrom $239Free CancellationRating
8.1
8.3

Boarding

8.0

Comfort

8.6

Crew

7.2

Entertainment

7.2

Food

Reviews

Easy flight to Mexico. Sat in row behind premium seats and had plenty of legroom. Flight attendants were pleasant.

1 / 10
Search Alaska Airlines flights
  • Alaska Airlines Flights From Chicago to Boston

    Alaska Airlines flight deals from Chicago to Boston start from $239 round-trip. Over the 27 Alaska Airlines flights for this route in a normal week, average airfare is usually $318 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, 410 ratings). Delta flies from Chicago to Boston around 20 times per week, with deals starting from $82 round-trip and rising to an average price of around $267.


United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets
United Airlines
Oct 26
ORD2:00 amChicago O'Hare Intl
2h 22m
BOS4:22 amBoston Logan Intl
Oct 26
BOS9:07 amBoston Logan Intl
2h 48m
ORD11:55 amChicago O'Hare Intl
United Airlines
Oct 28
ORD5:37 pmChicago O'Hare Intl
2h 23m
BOS8:00 pmBoston Logan Intl
Nov 5
BOS5:30 amBoston Logan Intl
2h 52m
ORD8:22 amChicago O'Hare Intl
United Airlines
Oct 27
ORD5:37 pmChicago O'Hare Intl
2h 23m
BOS8:00 pmBoston Logan Intl
Nov 1
BOS3:45 amBoston Logan Intl
2h 56m
ORD6:41 amChicago O'Hare Intl

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets
JetBlue
Oct 15
ORD2:45 pmChicago O'Hare Intl
2h 24m
BOS5:09 pmBoston Logan Intl
Oct 19
BOS7:15 amBoston Logan Intl
5h 04m
1 stop
ORD12:19 pmChicago O'Hare Intl
JetBlue
Oct 15
ORD2:45 pmChicago O'Hare Intl
2h 24m
BOS5:09 pmBoston Logan Intl
Oct 18
BOS11:55 amBoston Logan Intl
3h 02m
ORD2:57 pmChicago O'Hare Intl
JetBlue
Oct 28
ORD12:04 pmChicago O'Hare Intl
4h 46m
1 stop
BOS4:50 pmBoston Logan Intl
Oct 31
BOS12:10 pmBoston Logan Intl
3h 01m
ORD3:11 pmChicago O'Hare Intl

  • Are airlines flying from Chicago to Boston Logan Intl offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from Chicago to Boston Logan Intl, such as American Airlines, United Airlines, and JetBlue may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • 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.



Alternative routes for Chicago to Boston

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
St. Louis to Boston Flights
Fastest flight time2h 29m
Cheapest price$172
Chicago to Nantucket Flights
Fastest flight time4h 08m
Cheapest price$411
Chicago to Provincetown Flights
Fastest flight time12h 21m
Cheapest price$1,007

Similar Chicago to Boston flights

Flexible with your destination? Broaden your search and find flights similar to your Chicago to Boston route

Why use momondo?

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