American Airlines Flights from Boston (BOS) to Chicago (ORD)
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American Airlines Flights from BOS to ORD
How much is a American Airlines flight from Boston (BOS) to Chicago (ORD)?
One-way flights start as little as and there are roundtrips available from . Get in! You can score some sweet deals with Wotif and American Airlines.
How many non-stop American Airlines flights from Boston (BOS) to Chicago (ORD) are there per day?
American Airlines flies flights direct every day between Boston (BOS) and Chicago (ORD).
How far is Boston (BOS) from Chicago (ORD)?
It’s from Boston (BOS) to Chicago (ORD).
What is the best airline to fly from Logan Intl.?
At Wotif, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Logan Intl. with: .
Can I change or cancel my American Airlines tickets from Boston to Chicago on Wotif?
Change of plans? No worries! We’re right here to make things as easy as possible. Check out the American Airlines rules and restrictions in your itinerary. You can also use the No Change Fees filter to find flexible plane tickets for future trips. For more information on how to cancel or change your flight on Wotif, visit our customer service portal.
How do I find the best deal on American Airlines flights from Boston (BOS) to Chicago (ORD)?
Just review and compare all our awesome offers or enter your travel dates to see more terrific deals on American Airlines flights from Boston. And remember you can save even more when you bundle a hotel with your flight as part of a Wotif package. Sweet!
What’s a good way to get cheap American Airlines flight tickets from Boston to Chicago?
We have loads of cheap flights, so just enter your travel dates to see what’s available. If you can be flexible on when you fly, you’ll find even more epic flight deals. So get booking!
What is the cheapest time of year to fly from Boston (BOS) to Chicago (ORD)?
The cheapest time of the year for a return trip is . One-way, the cheapest month to fly is . Check our deal cards for details.
How long does it take to fly from BOS to ORD?
It typically takes hours to fly directly from Boston (BOS) to Chicago (ORD).
Epic Hotel in Chicago
Hilton Chicago O'Hare Airport
Location is absolutely perfect. Tunnel connects you easily from the baggage claim area! However, our room was very cold and the temperature was hard to adjust. Granted, it was also January and it was probably 5° outside, but still, it was a little hard to sleep. The hotel is quiet despite being situated ...
Reviewed on 18 Jan 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Room we well kept, staff was mildly unresponsive. Food is waaaay overpriced, but the free shuttle to the airport is clutch
Reviewed on 16 Jan 2026
Hyatt Regency O'Hare Chicago
Great Hospitality!!!
Reviewed on 19 Jan 2026
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Domestic to International Routes
- San Francisco to Dallas (SFO - DFW)
- Denver to Boston (DEN - BOS)
- San Francisco to Oslo (SFO - OSL)
- Tokyo to Washington (HND - IAD)
- Ontario to Santiago (ONT - SCL)
- Nashville to San Diego (BNA - SAN)
- Ontario to Santiago (ONT - SCL)
- Salt Lake City to Eugene (SLC - EUG)
- London to New York (LHR - LGA)
- Auckland to Glasgow (AKL - GLA)
Domestic Routes
- Nashville to Albany (BNA - ALB)
- Honolulu to Orange County (HNL - SNA)
- Nashville to Albany (BNA - ALB)
- Auckland to Los Angeles (AKL - LAX)
- Auckland to Glasgow (AKL - GLA)
- San Francisco to Oslo (SFO - OSL)
- Salt Lake City to Washington (SLC - DCA)
- San Francisco to Dallas (SFO - DFW)
- Denver to Boston (DEN - BOS)
- Nashville to San Diego (BNA - SAN)
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^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.