Cheap flights from Chicago to Boston

Round-trip
Economy
Chicago (CHI)
Boston (BOS)
Fri 2/26
Fri 3/5
Any month
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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 $64 The best flight deal from Chicago to Boston found on momondo in the last 72 hours is $64
Fastest flight time 2h 9m The fastest flight from Chicago to Boston takes 2h 9m.
Direct flights None There are no direct flights from Chicago to Boston. Popular non-direct routes for this connection are Chicago Midway - Boston Logan Intl and Chicago O'Hare Intl - Boston Logan Intl.
Airports in Boston 1 airport There is 1 airport near Boston: Boston Logan Intl (BOS)

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?
August
The cheapest time of year to fly to Boston from Chicago is August. Most expensive is December
What is the cheapest day to depart Chicago for Boston?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Sunday
When is the cheapest time to fly from Chicago to Boston?
at noon
Chicago to Boston flights are approximately 30% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Boston from Chicago?
Spirit Airlines
Spirit Airlines, Delta, and Envoy Air 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?
5 days before
The cheapest time to buy a flight from Chicago to Boston is approximately 5 days to departure
60
Days before departure
0

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
Spirit Airlines
Apr 28
2h 23m
Chicago O'Hare Intl
2h 23m
1:45 pm
Boston Logan Intl
May 2
8:47 am
Boston Logan Intl
2h 50m
11:37 am
Chicago O'Hare Intl
Major Airline
Feb 23
2h 18m
Chicago O'Hare Intl
2h 18m
1:57 pm
Boston Logan Intl
Mar 2
8:45 am
Boston Logan Intl
3h 09m
11:54 am
Chicago O'Hare Intl
Multiple Airlines
Feb 3
6h 14m
Chicago O'Hare Intl
6h 14m
1 stop
7:34 am
Boston Logan Intl
Feb 5
3:53 am
Boston Logan Intl
2h 57m
6:50 am
Chicago 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 Spirit Airlines
American Airlines
Feb 24
2h 18m
Chicago O'Hare Intl
2h 18m
1:57 pm
Boston Logan Intl
Spirit Airlines
Apr 17
2h 23m
Chicago O'Hare Intl
2h 23m
1:45 pm
Boston Logan Intl
Spirit Airlines
Feb 14
7h 25m
Chicago O'Hare Intl
7h 25m
1 stop
4:34 pm
Boston Logan Intl

Best airlines flying from Chicago to Boston

Compare and see reviews for airlines that fly from Chicago to Boston with momondo
AirlineRatingFree CancellationPrice
Delta
PriceFrom $48
Free Cancellation
Rating
8.3
8.2

Boarding

8.5

Comfort

8.8

Crew

7.8

Entertainment

8.1

Food

Reviews

Pros: I appreciate the choice of snacks.

Cons: The coffee served on the flight was lukewarm.

1 / 9
Spirit Airlines
PriceFrom $54
Free Cancellation
Rating
7.3
7.3

Boarding

7.3

Comfort

7.3

Crew

7.3

Entertainment

7.3

Food

Reviews

Pros: We made it safely

Cons: Awful experience. Early in the day I received several updates about my flight being delayed. No details on why, but much appreciated. Upon arriving to the airport the flight was still showing 59 mins delayed. Oddly, with all of the early communxaruin, it suddenly ceased! No communication for at least 2 hrs before the flight. Even as the 'would be' boarding window, the line formed with people asking questions... yet there were no answers or updates to the proposed time of departure. Even when the 59 min late departure came and went, there was NO communication. Folks were in an uproar! Finally, with no announcement, the gate attendant just started checking boarding passes and letting people go through the gate. Huh? I have zone 1, yet he said, we're just boarding everybody.... and, on the 3+ hr flight, only 1 bathroom worked. AWFUL EXPERIENCE!!!

1 / 1
JetBlue
PriceFrom $71
Free Cancellation
Rating
8.7
9.0

Boarding

9.0

Comfort

8.9

Crew

8.3

Entertainment

8.6

Food

Reviews

Cons: Todo fue Exelente...

1 / 4
United Airlines
PriceFrom $76
Free Cancellation
Rating
6.6
6.4

Boarding

7.0

Comfort

7.3

Crew

6.0

Entertainment

6.6

Food

Reviews

Pros: It was meh....

Cons: I got no notification that the flight was going to be 1 hour earlier

1 / 6
American Airlines
PriceFrom $76
Free Cancellation
Rating
7.2
7.9

Boarding

7.0

Comfort

7.7

Crew

7.4

Entertainment

6.4

Food

Reviews

Pros: Entertainment

Cons: The seat space/leg room is tiny. I found it impossible to fall asleep, being in the middle of a row of three with two "big" people in either side.

1 / 8
Southwest
PriceFrom $189
Free Cancellation
Rating
10.0

Which airlines flying from Chicago to Boston Logan Intl have COVID-19 safety policies in place?

Delta has implemented additional safety measures to accommodate travelers. Usage of HEPA filters, scheduled sanitation, enhanced cleaning of aircrafts, pre-flight testing, and mask policies are some of the implemented practices made by airlines to help keep you safe as you depart from Chicago to Boston Logan Intl. Keep in mind that policies will vary by airline.

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 Spirit Airlines may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.


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
Chicago to Provincetown Flights
Fastest flight time
10h 40m
Cheapest price
$268
Chicago to Nantucket Flights
Fastest flight time
12h 11m
Cheapest price
$288

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