Find cheap flight tickets from Boston (BOS) to Chicago (ORD). Cheapest fare starts from $233.
Boston
BOS
→
Chicago
ORD
10/14/2025 – 10/21/2025
Cheap flight deals from Boston to Chicago
Average price start from:
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$147
Round-trip flights from Boston to Chicago starting at $147. Book now for the best deals!
One-way from:
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$79
One-way flights from Boston to Chicago starting at $79. Great for flexible travel!
Cheapest day:
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Thursday
Thursday is the cheapest day to fly from Boston to Chicago. Save more by booking on this day!
Cheapest In:
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$63
Aug 2025
Aug 2025 is the cheapest month to fly from Boston to Chicago with prices starting at $63.
Find flight deals from Boston to Chicago
Cheapest flights from Boston to Chicago
ONEWAY FLIGHTS
LAST MINUTE
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Explore the cheapest oneway flights from Boston to Chicago spotted daily.
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$79
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$80
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$82
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$84
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$100
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$107
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$150
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$153
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$168
Non-stop • 60 min
BOS
Boston
BOS - Boston • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$222
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
If your flying dates are flexible, consider flying to Chicago on a Thursday.
Monthly Price Trends
Lowest fares from Boston to Chicago typically available in September.
Weather & Climate Information
Temperature
Chicago experiences cold winters with temperatures averaging 20°F to 30°F, while summers are warm, ranging from 70°F to 90°F. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and humidity is lower.
Rainfall
The best time to visit Chicago is from late spring to early fall, particularly May through September, when the weather is warm and pleasant. This period also coincides with vibrant local events like the Chicago Blues Festival and Lollapalooza, providing a lively atmosphere for tourists.
Airlines at Chicago
Experience seamless travel from Boston to Chicago with trusted airlines like Spirit Airlines, Frontier Airlines, Delta Air Lines, United Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers.
Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Boston to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.
Places to Visit in Chicago
Chicago, the Windy City, captivates with its stunning skyline and vibrant energy, where architectural marvels like the Willis Tower and the historic Chicago Water Tower tell tales of resilience and innovation. Dive into its rich cultural tapestry at the Art Institute, home to masterpieces, or indulge in the city’s iconic deep-dish pizza while soaking in the lively atmosphere of Millennium Park. Visitors can expect a symphony of experiences, from world-class museums to the rhythm of blues and jazz spilling from intimate venues, making Chicago a dynamic destination that leaves an indelible mark on every traveler.
About Chicago
Explore the wonders of Chicago on your journey from Boston. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Airlines Flying from Boston to Chicago
Experience seamless travel from Boston to Chicago with trusted airlines like Spirit Airlines, Frontier Airlines, Delta Air Lines, United Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers.
Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Boston to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.
Hotels in Chicago
Accommodations near ORD Airport provide excellent connectivity for travelers visiting Chicago. Look for hotels with shuttle services and modern amenities.
About Chicago
Explore the wonders of Chicago on your journey from Boston. This remarkable destination blends cultural treasures with modern amenities, creating an enriching travel experience. Consider visiting during off-peak seasons for better value and fewer crowds.
Places to Visit in Chicago
Chicago, the Windy City, captivates with its stunning skyline and vibrant energy, where architectural marvels like the Willis Tower and the historic Chicago Water Tower tell tales of resilience and innovation. Dive into its rich cultural tapestry at the Art Institute, home to masterpieces, or indulge in the city’s iconic deep-dish pizza while soaking in the lively atmosphere of Millennium Park. Visitors can expect a symphony of experiences, from world-class museums to the rhythm of blues and jazz spilling from intimate venues, making Chicago a dynamic destination that leaves an indelible mark on every traveler.
Hotels in Chicago
Accommodations near ORD Airport provide excellent connectivity for travelers visiting Chicago. Look for hotels with shuttle services and modern amenities.
Airlines Flying from Boston to Chicago
Experience seamless travel from Boston to Chicago with trusted airlines like Spirit Airlines, Frontier Airlines, Delta Air Lines, United Airlines. These carriers ensure reliable connections and flexible scheduling options for travelers.
Flight duration typically ranges around 10-15 hours, with most routes including one stopover in major aviation hubs. For your trip from Boston to Chicago, these airlines offer modern amenities and professional service to make your journey comfortable and enjoyable.
Frequently Asked Questions
How much does it cost to fly from Boston to Chicago?
Flight prices start from $79 for this route. Save more by booking during September and choosing Thursday departures.
What's the flight duration from Boston to Chicago?
The typical flight time is approximately 10-15 hours, with most routes featuring one stopover for better pricing and convenience.
What airlines serve the Boston to Chicago route?
Several airlines operate flights including Spirit Airlines, Frontier Airlines, Delta Air Lines. Compare schedules and prices to find the best option for your travel needs.
When should I book my flight for the best price?
For optimal savings, book 2-3 months ahead and consider traveling during September when demand is lower.
Where can I stay near ORD Airport?
There are several hotels near ORD Airport with convenient shuttle services. Many offer comfortable accommodations for both business and leisure travelers.
What makes Chicago worth visiting?
Chicago combines rich cultural heritage with modern attractions. Visit during pleasant weather months to experience the city at its best.
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