$185 Cheap flights from Logan International (BOS) to Chicago All Airport (CHI)

Lowest Prices
Uncover the best deals on BOS to CHI flights by comparing fares from hundreds of airlines and agencies.

New Deals Everyday
Get the best prices on BOS to CHI flights—we update our fares daily so you never miss a saving.

Best Travel Options
Compare hundreds of BOS to CHI flights and secure the best deals—we never add any service fees.

Cheap flights from Boston to Chicago (BOS to CHI)

Looking for a cheap last-minute deal or the best round-trip flight from Boston to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

Good to know

Useful information for finding cheap flights from Logan International to Chicago All Airport and booking your next trip

Cheapest Round Trip Flight

$185

American Airlines • 1 stop • 11h 46m

Aug 20 – Aug 24

The cheapest round trip flight from Logan International to Chicago All Airport is currently $185

🔍 Search Flights

Fastest Flight

4h 11m

The fastest nonstop flight from Logan International to Chicago All Airport takes 4h 11m

Recent airfare deals on Boston to Chicago

Aug 20 - Aug 24, Economy

Boston → Chicago

11h 46m

9:22 AM - 3:28 PM • 1 stop

Boston → Chicago

3h 48m

6:15 AM - 9:43 AM • nonstop

$185

American Airlines

Aug 20 - Aug 24, Economy

Boston → Chicago

15h 44m

11:56 AM - 8:40 PM • 1 stop

Boston → Chicago

30h 1m

3:29 PM - 10:30 AM • 1 stop

$223

Spirit Airlines

Aug 20 - Aug 24, Economy

Boston → Chicago

22h 16m

8:02 PM - 8:38 AM • 1 stop

Boston → Chicago

10h 24m

6:00 AM - 1:24 PM • 1 stop

$234

United Airlines

Aug 20 - Aug 24, Economy

Boston → Chicago

4h 11m

11:34 AM - 1:25 PM • nonstop

Boston → Chicago

9h 13m

5:00 PM - 11:53 PM • 1 stop

$240

Delta Airlines

Aug 20 - Aug 24, Economy

Boston → Chicago

4h 15m

7:20 AM - 9:15 AM • nonstop

Boston → Chicago

8h 43m

11:00 AM - 5:23 PM • 1 stop

$277

Delta Airlines

Aug 20 - Aug 24, Economy

Boston → Chicago

17h 20m

7:05 AM - 4:45 PM • 1 stop

Boston → Chicago

18h 45m

12:40 PM - 1:05 AM • 1 stop

$293

Southwest Airlines

Facts to know while booking flights from Boston to Chicago

What are the airports in Boston?

BOS

What’s the most popular airline flying from BOS to CHI?

The most popular airline flying from Boston to Chicago are

Can I fly from BOS to CHI non-stop?

Yes, you can fly BOS to CHI non-stop on

Which airlines fly nonstop between Boston and Chicago?

The non-stop flights between Boston and Chicago are .

What’s the earliest departure time from BOS to CHI Airport?

The earliest flight leaves BOS at 7:05 am and lands in CHI - Chicago All Airport

What are the airports in Chicago?

ORD,MDW

Can I make changes to my Boston to Chicago flight tickets or cancel them on FareLeaders.com?

No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.

Can I cancel my flight tickets from BOS to CHI?

Read the fare rules of the Boston to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.

Which airline alliances offer flights from Boston and Chicago?

operate flights between Boston and Chicago

How long does a flight from Boston to Chicago take?

It takes approximately 2 hour to fly non-stop from BOS to CHI, which is 866.65 miles by air.

Which airlines provide the cheapest flights from Boston (BOS) to Chicago (CHI) ?

In the past couple of days, the cheapest tickets to CHI from BOS were found on ('WN') : USD 293

Do I need a passport to fly between BOS and CHI?

What’s the latest departure time from BOS to CHI ?

The last flight leaves BOS at 8:02 pm