
Book Cheap American Airlines flight from Boston (BOS) to Chicago (ORD) from CA $90
Find The Best Day to Book a Cheap American Airlines Flights From Boston to Chicago
Cheapest American Airlines Flights from Boston (BOS) to Chicago (ORD)
The cheapest flights to O'Hare Intl. found within the past 7 days were CA $180 round trip and CA $90 one way. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Grab a great American Airlines flight from BOS to ORD
To find a great deal on American Airlines flights with Travelocity, simply enter your origin and destination airports, pick your travel dates, and hit search. From here, you can sort by price, flight duration, and arrival/departure time. You can also filter to find nonstop flights.
Flying American Airlines Boston to Chicago gives you fights to choose from. With that direct flight time of , you’ll be touching down before you know it.
Find cheap flights with American Airlines between Boston and Chicago
American Airlines has a range of great fares on stacks of flights, and to find the most affordable for you, there are a few tricks you can try. Booking in advance, for example, is a great way to grab a fantastic deal. Also, choose the cheapest month, if you can. One-way flights from Boston to Chicago with American Airlines are October.
The more flexible you are, the more affordable flights you’re likely to find. Consider one-way flights and connecting flights, as well as standard roundtrip and direct options. Even if you’re flying today, cheap last-minute flights are easy to find by entering your travel dates and hitting search.
Reasons to book your American Airlines flights with Travelocity
Travelocity makes it easy to book a seat, anywhere in the world. The vast inventory, fast search, and advanced filters put some of the best deals on the planet in one place. Whether you’re traveling on business, with friends, family, or on your own, take your pick from some fantastic options. And with free cancellation and pay later options, you can travel more and worry less.
Airport code | Country | Airport name | Number of flights |
|---|---|---|---|
| DFW | USA | Dallas-Fort Worth Intl. | 599 |
| CLT | USA | Charlotte-Douglas Intl. | 536 |
| ORD | USA | O'Hare Intl. | 317 |
| PHL | USA | Philadelphia Intl. | 247 |
| MIA | USA | Miami Intl. | 193 |
| DCA | USA | Ronald Reagan Washington National | 152 |
| PHX | USA | Sky Harbor Intl. | 141 |
| LAX | USA | Los Angeles Intl. | 81 |
| LGA | USA | LaGuardia | 72 |
| BOS | USA | Logan Intl. | 57 |
Travelers ❤️ these 🏨 after their flight to Chicago

Hilton Chicago O'Hare Airport
Very nice staff and a quick service.
Reviewed on Oct 22, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG
Got stuck in Chicago so needed a place to stay. The staff was friendly, they offer a free shuttle service, have a large restaurant on site, and everything was clean. Would recommend!
Reviewed on Oct 27, 2025

Hyatt Regency O'Hare Chicago
Yes
Reviewed on Oct 25, 2025
Want more than a(n) American Airlines Flight from Boston to Chicago?
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