Explore flight options from Windsor Locks to Chicago with competitive pricing starting from $258.
Windsor Locks
BDL
→
Chicago
ORD
10/14/2025 – 10/21/2025
Cheap flight deals from Windsor Locks to Chicago
Average price start from:
i
$147
Round-trip flights from Windsor Locks to Chicago starting at $147. Book now for the best deals!
One-way from:
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$55
One-way flights from Windsor Locks to Chicago starting at $55. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from Windsor Locks to Chicago. Save more by booking on this day!
Cheapest In:
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$137
Jun 2025
Jun 2025 is the cheapest month to fly from Windsor Locks to Chicago with prices starting at $137.
Find flight deals from Windsor Locks to Chicago
Cheapest flights from Windsor Locks to Chicago
ONEWAY FLIGHTS
LAST MINUTE
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Explore the cheapest oneway flights from Windsor Locks to Chicago spotted daily.
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$55
Non-stop • 60 min
BTV
Windsor Locks
BTV - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$55
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$65
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
MKE
Unknown City
$66
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$74
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$76
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$78
Non-stop • 60 min
BTV
Windsor Locks
BTV - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
MSP
Unknown City
$79
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$84
Non-stop • 60 min
ALB
Windsor Locks
ALB - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$89
Non-stop • 60 min
BDL
Windsor Locks
BDL - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$89
Non-stop • 60 min
ALB
Windsor Locks
ALB - Windsor Locks • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$99
Non-stop • 60 min
Price Trends & Analysis
Monthly Price Trends
Lowest fares from Windsor Locks to Chicago typically available in February.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with cold winters averaging 20°F to 30°F and warm summers reaching 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 precipitation is moderate.
Rainfall
The best time to visit Chicago is from late spring to early fall, specifically May to September, when the weather is pleasant and ideal for outdoor activities. During this period, you can enjoy vibrant local events like the Chicago Blues Festival and the Chicago Air and Water Show, making your trip even more memorable.
Airlines at Chicago
Traveling from Windsor Locks to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Spirit Airlines, Sun Country Airlines, Frontier Airlines, United Airlines provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Windsor Locks to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Places to Visit in Chicago
Chicago, the Windy City, pulses with an electric energy that captivates every visitor. Marvel at the stunning skyline adorned with architectural masterpieces like the Willis Tower, then immerse yourself in the rich tapestry of culture at the Art Institute, home to world-renowned masterpieces. Stroll along the picturesque shores of Lake Michigan, savor deep-dish pizza, and embrace the vibrant music scene that echoes through historic jazz clubs, promising an unforgettable adventure that blends history, art, and culinary delights.
About Chicago
Explore the wonders of Chicago on your journey from Windsor Locks. 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 Windsor Locks to Chicago
Traveling from Windsor Locks to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Spirit Airlines, Sun Country Airlines, Frontier Airlines, United Airlines provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Windsor Locks to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
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 Windsor Locks. 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, pulses with an electric energy that captivates every visitor. Marvel at the stunning skyline adorned with architectural masterpieces like the Willis Tower, then immerse yourself in the rich tapestry of culture at the Art Institute, home to world-renowned masterpieces. Stroll along the picturesque shores of Lake Michigan, savor deep-dish pizza, and embrace the vibrant music scene that echoes through historic jazz clubs, promising an unforgettable adventure that blends history, art, and culinary delights.
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 Windsor Locks to Chicago
Traveling from Windsor Locks to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Spirit Airlines, Sun Country Airlines, Frontier Airlines, United Airlines provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Windsor Locks to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Frequently Asked Questions
How much does it cost to fly from Windsor Locks to Chicago?
Flight prices start from $55 for this route. Save more by booking during February and choosing Wednesday departures.
What's the flight duration from Windsor Locks 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 Windsor Locks to Chicago route?
Several airlines operate flights including Spirit Airlines, Sun Country Airlines, Frontier Airlines. 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 February 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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