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Cheap flights from Boston to Chicago (BOS - CHI)

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The best prices from Boston to Chicago are usually found in February or September, booked 54 days in advance, depart on a Saturday or Tuesday and return on a Saturday

BOS - CHI
Price
$157 - $224
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches
Popular in July High demand for flights, 16% potential price rise
Cheapest in February Best time to find cheap flights, 16% potential price drop
Average price $206 Average for round-trip flights in April 2020
Round-trip from $157 From Boston to Chicago

Cheap flights from Boston to Chicago in April 2020

The best prices found for BOS to ORD flights for April
24 Apr - 26 Apr
$35pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
8 Apr - 30 Apr
$36pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
22 Apr - 25 Apr
$38pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

Boston to Chicago 2020 flight deals

Cheap flights to Chicago from Boston found for this year
18 May - 21 May
$33pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
16 May - 18 May
$35pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
20 May - 24 May
$37pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
18 May - 21 May
$33pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
24 Apr - 26 Apr
$35pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
22 Apr - 25 Apr
$38pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

Last minute flights from Boston to Chicago

Late deals on round-trip flights to Chicago from Boston, departing today and this week
8 Apr - 30 Apr
$36pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
5 Apr - 26 Apr
$44pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
3 Apr - 5 Apr
$52pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

One-way flights to Chicago from Boston

The cheapest one-way flights from Boston to Chicago
12:51 pm - 2:48 pm
Spirit Airlines
Nonstop
2h 57m
BOS - ORD
Spirit Airlines
$44
StudentUniverse
5:10 am - 7:07 am
Delta
Nonstop
2h 57m
BOS - ORD
Delta
$59
Delta
2:13 pm - 3:56 pm
JetBlue
Nonstop
2h 43m
BOS - ORD
JetBlue

Alternative routes for Boston to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Boston to Chicago
Flight duration
2h 38m
Average temperature for April in Chicago
62.6 °F
Avg rainfall for April in Chicago
2.3 ″

Airports servicing Boston

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)
Weekly flight availability
from Boston to Chicago
Sunday
43 daily flights
Monday
66 daily flights
Tuesday
61 daily flights
Wednesday
52 daily flights
Thursday
67 daily flights
Friday
62 daily flights
Saturday
40 daily flights

Related info for your journey

Useful info, stats and facts about Boston to Chicago flights.

Flight FAQs

From Boston to Chicago

Are flight prices decreasing from Boston to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Boston and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Boston to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Boston to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $35, but on average you can expect to pay $36.

Are there nonstop flights from Boston to Chicago for under $100 on Cheapflights?

Cheapflights has 3 direct flights from Boston to Chicago under $100. A good price for a nonstop flight from Boston to Chicago is less than $38.

Are there last-minute flights available from Boston to Chicago for under $100?

There are currently just 3 open flights from Boston to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from Boston to Chicago?

Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

This flight path from Boston Logan Intl to Chicago was viewed by 148 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What percent of flights are delayed?

Flights from Boston to Chicago are usually delayed by 73min. so prepare accordingly.

What is the cheapest airline for this route?

The cheapest airline for this route is American Airlines Inc.. When flying this airline from Boston to Chicago on average you can expect to find 214 flights available for this route daily.

How long does the flight from Boston to Chicago take?

A nonstop flight takes up to 3 hours, covering a distance of 536 miles.

How many flights depart from Boston to Chicago on average per day?

On average, you can expect to see 166 flights from Boston Logan Intl to Chicago a day.
Early Morning (Midnight to 6am) - 13% of flight departures
Morning (6am - Noon) - 40% of flight departures
Afternoon (Noon - 6pm) - 30% of flight departures
Evening (6pm - Midnight) - 17% of flight departures

Is Boston weather warmer or cooler than Chicago?

We forecast the temperature to be around the 84 °F's in July, on average. The temperature in Chicago is generally the same as in Boston. Book flights in a timely manner in correlation to your departure date.