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Cheap Flights from Boston to Chicago (BOS-ORD)
Prices were available within the past 7 days and start at $49 for one-way flights and $108 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Frequently asked questions
Travel information
Travel information
Origin airport | Logan Intl. |
Destination airport | O'Hare Intl. |
Airlines serving | American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United |
Roundtrip price | $107 |
Distance | 863 mi |
Book with confidence
Book with confidence
The cheapest times to fly from Boston to Chicago
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Boston to Chicago are during the month of May. You can find some of the cheapest flights from Boston to Chicago with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Boston to Chicago
Sunday is one of the best days to book for cheap flights from Boston to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Boston to Chicago
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Boston to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $49 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Boston to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Boston to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
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Flights
- JetBlue Airways
- Air France
- American Airlines
- Turkish Airlines
- Swiss International Air Lines
- British Airways
- United
- Frontier Airlines
- Lufthansa
- Spirit Airlines
- TAP Portugal
- Alaska Airlines
- Air Canada
- Delta
- KLM
- Iberia
- JetBlue Airways Boston (BOS) to Washington (DCA) flights
- JetBlue Airways Boston (BOS) to Oranjestad (AUA) flights
- Spirit Airlines Boston (BOS) to New Orleans (MSY) flights
- American Airlines Boston (BOS) to Guatemala City (GUA) flights
- JetBlue Airways Boston (BOS) to Santo Domingo (SDQ) flights
- Spirit Airlines New York (LGA) to Chicago (ORD) flights
- JetBlue Airways New York (JFK) to Chicago (ORD) flights
- Delta Dallas (DAL) to Chicago (ORD) flights
- Spirit Airlines Charlotte (CLT) to Chicago (ORD) flights
- Alaska Airlines Phoenix (PHX) to Chicago (ORD) flights
- Spirit Airlines Tampa (TPA) to Chicago (ORD) flights
- Frontier Airlines Denver (DEN) to Chicago (ORD) flights
- Alaska Airlines Los Angeles (LAX) to Chicago (ORD) flights
- American Airlines Miami (MIA) to Chicago (ORD) flights
- JetBlue Airways Fort Lauderdale (FLL) to Chicago (ORD) flights
- JetBlue Airways Boston (BOS) to Los Angeles (LAX) flights
- JetBlue Airways Boston (BOS) to Fort Lauderdale (FLL) flights
- JetBlue Airways Boston (BOS) to Tampa (TPA) flights
- JetBlue Airways Boston (BOS) to Punta Cana (PUJ) flights
- Alaska Airlines Boston (BOS) to Honolulu (HNL) flights
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- Flights from Boston (BOS) to Washington (DCA)
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- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Boston (BOS) to Orlando (MCO)
- Flights from Philadelphia (PHL) to Orlando (MCO)
- Flights from Boston (BOS) to Oranjestad (AUA)
- Flights from Boston (BOS) to New Orleans (MSY)
- Flights from Boston (BOS) to Guatemala City (GUA)
- Flights from Boston (BOS) to Paris (CDG)
- Flights from Los Angeles (LAX) to Seattle (SEA)
- Flights from Boston (BOS) to Santo Domingo (SDQ)
- Flights from Phoenix (PHX) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from Fort Lauderdale (FLL) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Denver (DEN) to Chicago (ORD)
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- Flights from Chicago (ORD) to Los Angeles (LAX)
- Flights from Boston (BOS) to Los Angeles (LAX)
- Flights from New York (NYC) to Los Angeles (LAX)
- Flights from Dallas (DFW) to Los Angeles (LAX)
- Flights from Seattle (SEA) to Los Angeles (LAX)
- Flights from Las Vegas (LAS) to Los Angeles (LAX)
- Flights from Boston (BOS) to Miami (MIA)
- Flights from Chicago (ORD) to Miami (MIA)
- Flights from Los Angeles (LAX) to New York (NYC)
- Flights from Miami (MIA) to New York (NYC)
- Flights from Atlanta (ATL) to New York (NYC)
- Flights from Dallas (DFW) to New York (NYC)
- Flights from Boston (BOS) to Fort Lauderdale (FLL)
- Flights from Boston (BOS) to Tampa (TPA)
- Flights from Portland (PDX) to Las Vegas (LAS)
- Flights from Dallas (DFW) to Las Vegas (LAS)
- Flights from Minneapolis (MSP) to Las Vegas (LAS)
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- Flights from Chicago (ORD) to Las Vegas (LAS)
- Flights from Houston (IAH) to Las Vegas (LAS)
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- Flights from Detroit (DTW) to Las Vegas (LAS)
- Flights from San Francisco (SFO) to Las Vegas (LAS)
- Flights from Seattle (SEA) to Las Vegas (LAS)
- Flights from Boston (BOS) to Punta Cana (PUJ)
- Flights from Boston (BOS) to Honolulu (HNL)
- Flights from Los Angeles (LAX) to Dallas (DFW)