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Cheap Flights from Boston to Chicago (BOS-CHI)
Prices were available within the past 7 days and start at S$129 for one-way flights and S$220 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, 3 Jun - Wed, 12 Jun
BOS
Boston
ORD
Chicago
S$220 Return, found 11 hours ago
S$220
Return
found 11 hours ago
Wed, 28 Aug - Sat, 7 Sep
BOS
Boston
ORD
Chicago
S$223 Return, found 4 days ago
S$223
Return
found 4 days ago
Tue, 11 Jun - Tue, 18 Jun
BOS
Boston
ORD
Chicago
S$235 Return, found 1 day ago
S$235
Return
found 1 day ago
Tue, 11 Jun - Tue, 18 Jun
BOS
Boston
ORD
Chicago
S$236 Return, found 1 day ago
S$236
Return
found 1 day ago
Tue, 11 Jun - Tue, 18 Jun
BOS
Boston
ORD
Chicago
S$249 Return, found 1 day ago
S$249
Return
found 1 day ago
Sat, 14 Sep - Sat, 28 Sep
BOS
Boston
ORD
Chicago
S$258 Return, found 4 days ago
S$258
Return
found 4 days ago
Tue, 11 Jun - Tue, 18 Jun
BOS
Boston
ORD
Chicago
S$262 Return, found 1 day ago
S$262
Return
found 1 day ago
Mon, 3 Jun - Wed, 12 Jun
BOS
Boston
ORD
Chicago
S$269 Return, found 11 hours ago
S$269
Return
found 11 hours ago
Mon, 3 Jun - Wed, 12 Jun
BOS
Boston
ORD
Chicago
S$270 Return, found 11 hours ago
S$270
Return
found 11 hours ago
Tue, 11 Jun - Tue, 18 Jun
BOS
Boston
ORD
Chicago
S$270 Return, found 1 day ago
S$270
Return
found 1 day ago
Origin airport | Logan Intl. |
Destination airport | O'Hare Intl. |
Return price | S$220 |
Distance | 1381 km |
Perfect flights from Boston to Chicago
Your Journey from Boston to Chicago
Start your unforgettable journey with Expedia. Our broad selection of flights from Boston to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
Choosing Your Ideal Flight
With Expedia, you have access to a wide range of airlines, including Delta, United. Our selection of flights from Logan Intl. to CHI-All Airports caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
Maximizing Value with Boston to Chicago Flights
Experience the joy of finding cheap flights from Logan Intl. to CHI-All Airports that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$129 and roundtrip prices from S$220*.
Pre-Flight Essentials
Ensure a smooth journey from Boston to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
Experience the Vibrant Chicago
Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
Added Convenience on Your Boston to Chicago Flight
Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Boston to Chicago.
Beyond the Flight – Exploring Chicago
With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
Book Your Flight from Boston to Chicago with Confidence
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Boston to Chicago with confidence. Book your travel arrangements with Expedia today.
*Note: Prices may vary based on availability and are subject to change.
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Chicago Airports
Chicago
S$219.70
Milwaukee
S$409.00
Flights
San Francisco to Grand Canyon (SFO - GCN)Boston to San Francisco (BOS - SFO)Singapore to Seattle (SIN - SEA)San Diego to San Francisco (SAN - SFO)Seattle to San Francisco (SEA - SFO)Singapore to Philadelphia (SIN - PHL)New York to Singapore (NYC - SIN)Dallas to Singapore (DFW - SIN)New York to Toronto (NYC - YYZ)San Diego to Las Vegas (SAN - LAS)Boston to Singapore (BOS - SIN)New York to Cancun (NYC - CUN)Singapore to Boston (SIN - BOS)San Francisco to Las Vegas (SFO - LAS)Singapore to Fort Lauderdale (SIN - FLL)Los Angeles to Boston (LAX - BOS)Singapore to Dallas (SIN - DFW)San Francisco to Seattle (SFO - SEA)Pittsburgh to Newark (PIT - EWR)Singapore to St. Louis (SIN - STL)Toronto to New York (YYZ - NYC)Los Angeles to Las Vegas (LAX - LAS)New York to Boston (JFK - BOS)Los Angeles to New York (LAX - NYC)Las Vegas to San Francisco (LAS - SFO)New York to Denver (NYC - DEN)Singapore to San Diego (SIN - SAN)Singapore to Las Vegas (SIN - LAS)Singapore to Cleveland (SIN - CLE)New York to Los Angeles (NYC - LAX)
*Available to Expedia members.