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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 September or January, booked 56 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

Home North America USA Illinois Chicago Cheap flights from Boston to Chicago

How to find the cheapest flight from
Boston (BOS) to Chicago (CHI)

BOS - CHI
Price
$158 - $224
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches
Popular in July High demand for flights, 15% potential price rise
Cheapest in September Best time to find cheap flights, 17% potential price drop
Round-trip from $158 From Boston to Chicago
One-way from $41 One-way flight from Boston to Chicago
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Boston to Chicago?

Departing on a Friday is a good option for securing a great price. You can expect to save up to 20% when planning your travel around this day of the week.

How far in advance should I book a flight from Boston to Chicago?

To save up to 10% on this flight, we recommend booking at least 37 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Boston to Chicago from $177 1-2 weeks out and tickets from $177 for flights departing within the next 72 hours.

Cheap flights from Boston to Chicago in July, August 2020

The best prices found for BOS to CHI flights for July, August
29 Jul - 4 Aug
$32pp
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
15 Jul - 18 Aug
$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
29 Jul - 4 Aug
$40pp
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

Boston to Chicago 2020 flight deals

Cheap flights to Chicago from Boston found for this year
29 Jul - 4 Aug
$32pp
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
15 Jul - 18 Aug
$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
29 Jul - 4 Aug
$40pp
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

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
29 Jul - 4 Aug
$32pp
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
15 Jul - 19 Aug
$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 Jul - 29 Jul
$40pp
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
23 Jun - 7 Jul
$83pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
26 Jun - 14 Jul
$84pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
23 Jun - 7 Jul
$86pp
BOS
Boston Logan Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

One-way flights to Chicago from Boston

The cheapest one-way flights from Boston to Chicago
4:29 am - 6:19 am
JetBlue
Nonstop
2h 50m
BOS - ORD
JetBlue
$41
3:00 am - 4:58 am
Japan Airlines
Nonstop
2h 58m
BOS - ORD
Japan Airlines
$51
Ovago
4:00 am - 9:23 am
Aeromexico
1 Stop
6h 23m
BOS - ORD
Aeromexico
$59
Ovago

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 $32, but on average you can expect to pay $49.

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

Cheapflights has at least 20 direct flights from Boston to Chicago under $100. A good price for a nonstop flight from Boston to Chicago is less than $51.

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

There are currently 20+ 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: Tuesday.

How popular is this flight route?

This flight path from Boston Logan Intl to Chicago was viewed by 217 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

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 540 miles.

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

On average, you can expect to see 1 flight from Boston Logan Intl to Chicago a day.
Morning (6am - Noon) - 100% 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.

Related searches

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Alternative routes for Boston to Chicago

Boston to Bloomington from $183 pp

Destination information for Chicago

Things to know before you go. Useful info for your trip from Boston to Chicago
Flight duration
2h 37m
Average temperature for July in Chicago
84.2 °F
Avg rainfall for July in Chicago
3.7 ″

Airports servicing Boston

Boston (BOS)

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Chicago Midway (MDW)
Rockford (RFD)

Popular flight searches

Check out other popular destinations found by fellow travelers

Hourly flight availability from Boston to Chicago

Afternoon Noon to 6 PM 39% of BOS to CHI departures
Morning 6 AM to noon 38% of BOS to CHI departures
Early morning Midnight to 6 AM 23% of BOS to CHI departures
Evening 6 PM to midnight 0% of BOS to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Boston to Chicago
Sunday
28 daily flights
Monday
33 daily flights
Tuesday
17 daily flights
Wednesday
16 daily flights
Thursday
30 daily flights
Friday
32 daily flights
Saturday
17 daily flights