Cheap Flights from Boston to Chicago starting at S$ 48
Book one-way or return flights from Boston to Chicago from as little as S$ 48. Choose from the popular airlines below and book your flight today!
- One way
- Round-trip
- BOS06:1011h 25m1 stopORD16:35Wed, May 8|Boston - Chicago|Spirit AirlinesS$ 48S$ 8141% OFF41% OFFS$ 81S$ 48
- BOS07:002h 33mDirectORD08:33Thu, Jun 6|Boston - Chicago|Spirit AirlinesS$ 48S$ 8140% OFF40% OFFS$ 81S$ 48
- BOS07:002h 33mDirectORD08:33Tue, Jun 11|Boston - Chicago|Spirit AirlinesS$ 49S$ 8140% OFF40% OFFS$ 81S$ 49
- BOS07:002h 33mDirectORD08:33Wed, Jun 12|Boston - Chicago|Spirit AirlinesS$ 50S$ 50
- BOS05:0513h 41m1 stopORD17:46Tue, May 7|Boston - Chicago|Spirit AirlinesS$ 53S$ 53
- BOS06:252h 55mDirectORD08:20Tue, May 14|Boston - Chicago|Delta Air LinesS$ 57S$ 57
- BOS06:1011h 25m1 stopORD16:35Tue, May 14|Boston - Chicago|Spirit AirlinesS$ 58S$ 58
- BOS12:4611h 44m1 stopMDW23:30Wed, May 15|Boston - Chicago|Frontier AirlinesS$ 59S$ 59
- BOS12:4111h1 stopMDW22:41Sat, May 4|Boston - Chicago|Frontier AirlinesS$ 60S$ 60
- BOS12:4611h 44m1 stopMDW23:30Wed, May 8|Boston - Chicago|Frontier AirlinesS$ 60S$ 60
- BOS13:003h 5mDirectCHI14:00Fri, May 3|Boston - Chicago|Spirit AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Searching for the best last minute flight from Boston to Chicago? Find one-way or return flights that are affordable and fit your itinerary.
Trip.com monitors the ticket fares of flights from Boston to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.
View airlines operating flights from Boston to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Find more flights and airlines
Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Boston to Chicago.
- CheapestBOS05:0513h 41m1 transferORD17:46General Edward Lawrence Logan International Airport - O'Hare International AirportTue, May 7Spirit AirlinesS$ 53
- BOS12:4111h 0m1 transferMDW22:41General Edward Lawrence Logan International Airport - Midway International AirportSat, Apr 27Frontier AirlinesS$ 229
- BOS12:4111h 0m1 transferMDW22:41General Edward Lawrence Logan International Airport - Midway International AirportSat, Apr 27Frontier AirlinesS$ 229Find More Flights
Frequently Asked Questions
How to find a cheap flight from Boston to Chicago
Cheapest direct flight price | S$ 47 |
---|---|
Cheapest return ticket price | S$ 100 |
Cheapest month | December |
Peak season for travel | October |
Flight distance | 1,371.27km |
Average flight time | 2 hours 52 minutes |
Popular airline | American Airlines |
Plan Your Trip Around Chicago
Find Cheap Flights & Deals on Trip.com
Popular Flights from Boston
- Flights Boston to Hong Kong
- Flights Boston to Shanghai
- Flights Boston to Beijing
- Flights Boston to Orlando
- Flights Boston to Taipei
- Flights Boston to London
- Flights Boston to New York
- Flights Boston to San Francisco
- Flights Boston to Reykjavik
- Flights Boston to Toronto
- Flights Boston to Bangkok
- Flights Boston to Los Angeles
- Flights from General Edward Lawrence Logan International Airport to Billings
- Flights from General Edward Lawrence Logan International Airport to Singapore
- Flights from Boston to Chongqing Jiangbei International Airport
- Flights from Boston to Ordos Ejin Horo Airport
- Flights from Boston to ENY Airport
- Flights from Boston to Meilan International Airport
- Flights from Boston to Heihe Airport
- Flights from Boston to Hong Kong International Airport
- Flights from General Edward Lawrence Logan International Airport to Singapore Changi Airport
Recommended Hotels in Chicago
- Hotels near Art Institute of Chicago Columbus Drive Entrance
- Hotels near Muddy Waters Mural
- Hotels near Paradise Sauna
- Hotels near Mars Gallery
- Hotels near Museum of Holography,
- Hotels near Big Monster Toys
- Hotels near Norwood Park
- Hotels near Windy City Playhouse
- Hotels near Millennium Monument
- Hotels near Miró's Chicago (The Sun, The Moon, and One Star)
- Hotels near Benito Juarez Community Academy
- Hotels near ZARA
- Hotels near Imagination Station-Dramatic
- Hotels near The Park at Wrigley
- Hotels near Pearle Vision
- Hotels near North Park University
- Hotels near Riverwalk - 100 W
- Hotels near Lincoln Park
- Hotels near Chicago Auto Show
- Hotels near The Art Institute of Chicago
- Hotels near UIC College of Education
- Hotels near 7-Eleven
- Hotels near Wiggly Field Dog Park
- Hotels near Oliver Peoples
- Hotels near Boxville
- Hotels near Reva and David Logan Center for the Arts
- Hotels near And Studio
- Hotels near Oriole Park
- Hotels near New Birth Church-God In Christ
- Hotels near FoodSeum
Popular Flights to Chicago
- Flights Hong Kong to Chicago
- Flights Bangkok to Chicago
- Flights Seoul to Chicago
- Flights Shanghai to Chicago
- Flights New York to Chicago
- Flights Manila to Chicago
- Flights Tokyo to Chicago
- Flights Atlanta to Chicago
- Flights Singapore to Chicago
- Flights Istanbul to Chicago
- Flights Orlando to Chicago
- Flights Los Angeles to Chicago
- Flights from Singapore Changi Airport to Chicago
- Flights from Edinburgh Airport to Chicago
- Flights from Seletar Airport to Chicago
- Flights from Paine Field Airport to Chicago
- Flights from Lincoln Airport to Chicago
- Flights from University Park Airport to Chicago
- Flights from London to Chicago Rockford International Airport
- Flights from London to O'Hare International Airport
- Flights from London to Midway International Airport
- Flights from Tokyo to Midway International Airport
- Flights from Tokyo to O'Hare International Airport
- Flights from Sapporo to O'Hare International Airport
- Flights from Singapore Changi Airport to O'Hare International Airport
- Flights from Singapore Changi Airport to Midway International Airport
- Flights from Seletar Airport to O'Hare International Airport
Recommended Routes
- Flights Los Angeles to New York
- Flights New York to Los Angeles
- Flights San Francisco to Los Angeles
- Flights San Francisco to Las Vegas
- Flights Los Angeles to Las Vegas
- Flights Los Angeles to Honolulu
- Flights Las Vegas to San Francisco
- Flights San Francisco to New York
- Flights Los Angeles to San Francisco
- Flights New York to Orlando
- Flights New York to San Francisco
- Flights New York to Miami
- Flights from Los Angeles International Airport to Burbank
- Flights from Los Angeles International Airport to Santa Ana
- Flights from Los Angeles International Airport to Long Beach
- Flights from Orlando International Airport to Sarasota
- Flights from Orlando International Airport to Tampa
- Flights from Orlando International Airport to Gainesville
- Flights from San Francisco to Scotts Bluff County Airport
- Flights from San Francisco to WilkesBarre International Airport
- Flights from San Francisco to Chadron Municipal Airport
- Flights from San Francisco to Kalamazoo Airport
- Flights from San Francisco to Willard Airport
- Flights from San Francisco to Colorado Springs Airport
- Flights from Orlando International Airport to Tampa International Airport
- Flights from Paine Field Airport to Bishop
Site Operator: Trip.com Travel Singapore Pte. Ltd. Travel License No. 02943