Cheap flights from Boston to Chicago (BOS - CHI)

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The best prices from Boston to Chicago are usually found in August or July, booked 3 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

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

All the information you need to plan the best BOS to CHI flight in 2021: compare Boston to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
BOS - CHI
Price
$56 - $206
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

December

High demand for flights, 29% potential price rise

Cheapest in

August

Best time to find cheap flights, 62% potential price drop

Average price

$117

Average for round-trip flights in June 2021

Round-trip from

$56

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 20 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 $137 1-2 weeks out and tickets from $157 for flights departing within the next 72 hours.

What is the cheapest month to fly from Boston to Chicago?

The best pricing can be found in the month of April. Prices to Chicago from Boston average $135. You can even find prices in April for less than $135, as users have found deals to Chicago from as low as $33. The month of December appears to be one of the more expensive times to travel to Chicago from Boston. Flying in the targeted month can save you up to 49%.

When is the cheapest time to fly from Boston to Chicago (BOS - CHI)?

A simple way to save on the total cost of your ticket is to fly from Boston to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the afternoon.

Cheap flights from Boston to Chicago in June, July 2021

The best prices found for BOS to CHI flights for June, July
8 Jul - 15 Jul
$95pp
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
12 Jul - 15 Jul
$100pp
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
8 Jul - 12 Jul
$101pp
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

Boston to Chicago 2021 flight deals

Cheap flights to Chicago from Boston found for this year
18 Sep - 22 Sep
$49pp
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
14 Sep - 15 Sep
$50pp
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
11 Sep - 15 Sep
$53pp
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 Sep - 22 Sep
$49pp
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
14 Sep - 15 Sep
$50pp
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
11 Sep - 15 Sep
$53pp
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
29 Jun - 20 Jul
$124pp
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
29 Jun - 10 Aug
$125pp
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
30 Jun - 10 Jul
$150pp
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
2:56 am - 8:13 am
American Airlines
1 Stop
6h 17m
BOS - ORD
American Airlines
7:45 am - 1:18 pm
Allegiant Air
1 Stop
6h 33m
BOS - MDW
Allegiant Air
$78
Kiwi.com
1:35 am - 4:45 am
Delta
1 Stop
4h 10m
BOS - MDW
Delta
$80
Delta

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Boston</span> to <span class="emphasized">Chicago</span> 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.

Which airlines flying from Boston Logan Intl to Chicago have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and JetBlue are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

What airport do you fly from for flights from Boston to Chicago?

Located just 2.6 mi from the city center, Boston Logan Intl is the airport most travelers will use when flying to Chicago from Boston. Booking flights from Logan Intl (BOS) to Chicago should be relatively easy as there are 41 daily outbound flights to Chicago from 7 different airlines.

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 $49, but on average you can expect to pay $67.

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 $75.

Are there last-minute flights available from Boston to Chicago for under $200?

There are currently 20+ open flights from Boston to Chicago within the next 7 days for less than $200.

What days are nonstop flights available from Boston to Chicago?

Days when nonstop flights are available for this flight are: Saturday.

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

On average, you can expect to see 2 flights from Boston Logan Intl to Chicago a day.
Afternoon (Noon - 6pm) - 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.

How long is the flight from Boston to Chicago?

Departing from Boston to Chicago will take you 2h 33m. There are 869 mi between Boston and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

What is the cheapest airline to fly from Boston to Chicago round-trip?

Currently priced at $49, Spirit Airlines will fly you from Boston to Chicago and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. This flight start at 66% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Boston to Chicago one-way?

One-way options have recently been found by users for as low as $28 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $50 and Delta from $70 one-way.

Alternative routes for Boston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Boston to Chicago.
Flight duration
2h 26m
Average temperature for June in Chicago
78.8 °F
Avg rainfall for June in Chicago
3.4 ″

Airports servicing Boston

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Boston to Chicago

The chart below displays the airlines Cheapflights users traveling from Boston to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$56 $168 No cancel fee 65%
United Airlines
$80 $237 No cancel fee 69%
American Airlines
$77 $241 No cancel fee 71%
JetBlue
$71 $250 No cancel fee 62%
Delta
$68 $270 No cancel fee N/A
Southwest
$185 $387 No cancel fee 63%

Hourly flight availability from Boston to Chicago

See what time of day planes typically take off from Boston towards Chicago.
Morning 6 AM to noon 48% of BOS to CHI departures
Early morning Midnight to 6 AM 25% of BOS to CHI departures
Afternoon Noon to 6 PM 23% of BOS to CHI departures
Evening 6 PM to midnight 4% of BOS to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Boston to Chicago
See how many times per day planes take to the skies headed from Boston to Chicago.
Sunday
48 daily flights
Monday
42 daily flights
Tuesday
31 daily flights
Wednesday
35 daily flights
Thursday
42 daily flights
Friday
49 daily flights
Saturday
45 daily flights
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