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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

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

$45

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.

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 30% on your trip compared to booking a flight in the afternoon.

Cheap flights from Boston to Chicago in October, November 2020

The best prices found for BOS to CHI flights for October, November
18 Nov - 2 Dec
$49pp
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
10 Nov - 11 Nov
$59pp
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
10 Nov - 14 Nov
$66pp
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 2020 flight deals

Cheap flights to Chicago from Boston found for this year
10 Dec - 14 Dec
$48pp
BOS
Boston Logan Intl
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
BOS
Boston Logan Intl
2 Dec - 5 Dec
$49pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
BOS
Boston Logan Intl
3 Dec - 7 Dec
$50pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
BOS
Boston Logan Intl

Non-stop flights to Chicago from Boston

Save time with Boston to Chicago direct flight deals
16 Nov - 17 Nov
$86pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
14 Nov - 15 Nov
$89pp
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl
7 Nov - 7 Nov
$91pp
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American 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
4 Nov - 11 Nov
$72pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
4 Nov - 11 Nov
$79pp
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
3 Nov - 6 Nov
$80pp
BOS
Boston Logan Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl

One-way flights to Chicago from Boston

The cheapest one-way flights from Boston to Chicago
6:26 am - 8:10 am
United Airlines
Nonstop
2h 44m
BOS - ORD
United Airlines
$45
United
11:41 am - 1:41 pm
American Airlines
Nonstop
3h 00m
BOS - ORD
American Airlines
4:04 am - 5:56 am
JetBlue
Nonstop
2h 52m
BOS - ORD
JetBlue

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.

What safety measures are being taken by airlines flying from Boston Logan Intl to Chicago to control the spread of COVID-19?

JetBlue, Southwest, and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. Some of the new policies that have been implemented to accommodate travelers flying from Boston Logan Intl to Chicago are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

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.

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 $48, but on average you can expect to pay $68.

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 $114.

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: Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

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

On average, you can expect to see 25 flights from Boston Logan Intl to Chicago a day.
Early Morning (Midnight to 6am) - 24% of flight departures
Morning (6am - Noon) - 24% of flight departures
Afternoon (Noon - 6pm) - 52% 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 44m. There are 869 mi between Boston and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Boston to Chicago round-trip?

Currently priced at $48, 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. Check Cheapflights for deals on American Airlines for as low as $89. These flights start at 74% 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 $23 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $41 and American Airlines from $48 one-way.

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 34m
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing Boston

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Boston to Chicago

Morning 6 AM to noon 55% of BOS to CHI departures
Early morning Midnight to 6 AM 26% of BOS to CHI departures
Afternoon Noon to 6 PM 19% 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
34 daily flights
Monday
29 daily flights
Tuesday
16 daily flights
Wednesday
14 daily flights
Thursday
25 daily flights
Friday
30 daily flights
Saturday
18 daily flights
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