
Popular airlines from Logan International Airport (BOS) to Chicago O'Hare Intl. Airport (ORD)
- JetBlue Airways
JetBlue Airways
- Spirit Airlines
Spirit Airlines
- American Airlines
American Airlines
- Delta
Delta
- United
United
- Southwest Airlines
Southwest Airlines
- Frontier Airlines
Frontier Airlines
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Cheap Flights from Boston to Chicago (BOS-ORD)
Prices were available within the past 7 days and start at ¥8,610 for one-way flights and ¥17,230 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from Boston (BOS) to Chicago (ORD)
November is typically the cheapest month to fly
Origin airport | Logan Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, United |
Roundtrip price | ¥17,230 |
Distance | 1381 km |
Average flight time | 1 hour 49 mins |
Boston to Chicago Flights
Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Boston to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.
Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with BOS to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Boston for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.
All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.
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Top Routes from Boston
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Top Routes to Chicago
- Newark Liberty Intl. Airport to Chicago (EWR - ORD)
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