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Uncover the best deals on Boston to Chicago flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest BOS - ORD Flights
Useful information for finding best airline tickets from Logan International to Chicago O'Hare International on your next trip.
Cheapest Round Trip Flight
$502
American Airlines
• nonstop
• 5h 7m
Oct 09 – Oct 12
The cheapest round trip flight from Boston to Chicago (BOS-ORD-BOS) is currently $502
Cheapest One way Flight
$84
United Airlines
• 1 stop
• 10m
Aug 12
The cheapest one way flight from Boston to Chicago (BOS-ORD) is currently $84
Cheapest Direct Flight
$498
American Airlines
• nonstop
• 5h 5m
Oct 09
The cheapest nonstop flight from Boston to Chicago (BOS-ORD) is currently $498
Fastest Flight
10m
The fastest nonstop flight from Boston to Chicago (BOS-ORD) takes 10m
Top Airlines Flying from Boston to Chicago
Latest Flight Deals from Boston (BOS) to Chicago (ORD)
Compare and book low fare round-trip air tickets from Boston to Chicago. Ideal for travelers with confirmed return itineraries.
Oct 09 - Oct 12, Economy
Boston → Chicago
5h 7m
8:23 AM - 10:30 AM • nonstop
Boston → Chicago
3h 57m
6:00 AM - 9:37 AM • nonstop
American Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
10h 5m
6:00 AM - 11:05 AM • 1 stop
Boston → Chicago
3h 57m
6:00 AM - 9:37 AM • nonstop
American Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
5h 6m
7:23 PM - 9:29 PM • nonstop
Boston → Chicago
8h 29m
6:29 AM - 12:38 PM • 1 stop
American Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
4h 13m
10:36 AM - 12:29 PM • nonstop
Boston → Chicago
3h 43m
6:10 AM - 9:33 AM • nonstop
United Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
4h 19m
6:00 AM - 7:59 AM • nonstop
Boston → Chicago
3h 50m
9:24 PM - 12:54 AM • nonstop
United Airlines
Explore competitive one-way airfare options for BOS - ORD flights. Best suited for flexible or open-ended travel plans.
Flying to Chicago soon? We've surfaced some of the most affordable last-minute flights from Boston to Chicago, ideal for urgent plans or spontaneous trips.
Looking for the fastest way to Chicago? These direct flight options from BOS to ORD offer both convenience and value—no layovers, just straight to your destination.
Oct 09 - Oct 12, Economy
Boston → Chicago
5h 5m
3:31 PM - 5:36 PM • nonstop
Boston → Chicago
3h 57m
6:00 AM - 9:37 AM • nonstop
American Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
5h 7m
8:23 AM - 10:30 AM • nonstop
Boston → Chicago
3h 57m
6:00 AM - 9:37 AM • nonstop
American Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
5h 4m
10:29 AM - 12:33 PM • nonstop
Boston → Chicago
3h 57m
6:00 AM - 9:37 AM • nonstop
American Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
4h 13m
10:36 AM - 12:29 PM • nonstop
Boston → Chicago
3h 43m
6:10 AM - 9:33 AM • nonstop
United Airlines
Oct 09 - Oct 12, Economy
Boston → Chicago
4h 19m
6:00 AM - 7:59 AM • nonstop
Boston → Chicago
3h 50m
9:24 PM - 12:54 AM • nonstop
United Airlines
FAQs on Boston to Chicago Flights
What are the airports in Boston?
BOS
What’s the most popular airline flying from BOS to ORD?
The most popular airline flying from Boston to Chicago are
Can I fly from BOS to ORD non-stop?
Yes, you can fly BOS to ORD 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 ORD Airport?
The earliest flight leaves BOS at 6:00 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
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 ORD?
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 ORD, which is 866.65 miles by air.
Which airlines provide the cheapest flights from Boston (BOS) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from BOS were found on F9 : USD 218
Do I need a passport to fly between BOS and ORD?
No
What’s the latest departure time from BOS to ORD ?
The last flight leaves BOS at 7:23 pm
Boston (BOS) to Chicago (ORD): Airport Information
| Origin Airport | Logan International, Boston, US |
| Destination Airport | Chicago O'Hare International , Chicago, US |
| Distance | 867 miles |
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