$47 Cheap flight deals from Boston (BOS) to Chicago (CHI)
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This Weekend's Flight Deals from Boston to Chicago
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $47 One Way, $94 Round Trip from Boston to Chicago
Prices starting at $94 for return flights and $47 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages
Hotel Felix River North/Magnificent Mile
Jun 19 - Jun 23
Boston (BOS) to Chicago (ORD)
Chicago (ORD) to Boston (BOS)
Reviewed on May 1, 2025
Chicago packages with premium economy flights
Omni Chicago Hotel
Jul 4 - Jul 7
Boston (BOS) to Chicago (ORD)
Reviewed on May 9, 2025
More About Flying To Chicago from Boston
Route Information for Flights from Boston to Chicago
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Save on your Boston to Chicago flights with Orbitz deals. You'll have more dough leftover for sales on legendary pizza and bargain baseball tickets.
Manchester-Boston Regional Airport (MHT), three miles south of downtown Manchester, New Hampshire, offers daily domestic flights from Boston to Chicago. Southwest Airlines flies into Midway International Airport (MDW), and United Express discount flights from Boston to Chicago land at O'Hare (ORD). United Express low fare Boston to Chicago flights are operated by its partners ExpressJet, GoJet, and Trans States Airlines. Manchester Airport Access Road links the airport with the Everett Turnpike and U.S. Route 3. Bus transport to the Manchester central business district is provided by the Manchester Transit Authority. The Boston-Montreal route offered by Greyhound stops three times per day at MHT.
Northwest of the Loop, Chicago O'Hare International Airport is hub to United, Spirit, and American Airlines. Originally a World War II aircraft manufacturing plant, O'Hare was named for the U.S. Navy's first flying ace. Terminal 1 handles low cost United Airlines flights from Boston to Chicago. United also has three clubrooms, an international lounge, and an Arrivals Suite there. US Airways and Delta Airlines operate in Terminal 2. United has a development plan to redo its clubroom and put in more jet bridges. Terminal 3 is home to American Airlines and budget domestic carriers offering cheap Boston to Chicago flights. Terminal 5 handles international flights, except those arriving from locations with U.S. border preclearance.
Frequently asked questions
Flights to Chicago
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Flights from Boston
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.