Flights from Windsor Locks to Chicago from $55

Q: 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.

Q: 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.

Q: What airlines serve the Windsor Locks to Chicago route?

Several airlines operate flights including Southwest Airlines, Delta Air Lines, Frontier Airlines. Compare schedules and prices to find the best option for your travel needs.

Q: 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.

Q: 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.

Windsor Locks

BDL

→

Chicago

MDW

From

To

10/14/2025 – 10/21/2025

Travelers & Class

Include hotels in search

Cheap flight deals from Windsor Locks to Chicago

Average price start from:

i

$237

Round-trip flights from Windsor Locks to Chicago starting at $237. Book now for the best deals!

One-way from:

i

$55

One-way flights from Windsor Locks to Chicago starting at $55. Great for flexible travel!

Cheapest day:

i

Wednesday

Wednesday is the cheapest day to fly from Windsor Locks to Chicago. Save more by booking on this day!

Cheapest In:

i

January

Find the best month to travel from Windsor Locks to Chicago

Find flight deals from Windsor Locks to Chicago

Cheapest flights from Windsor Locks to Chicago

ONEWAY FLIGHTS

LAST MINUTE

CHEAP FLIGHTS

BEST FLIGHTS

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

MDW

Unknown City

$55

Non-stop • 60 min

BTV

Windsor Locks

BTV - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$85

Non-stop • 60 min

ALB

Windsor Locks

ALB - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$89

Non-stop • 60 min

BDL

Windsor Locks

BDL - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$89

Non-stop • 60 min

ALB

Windsor Locks

ALB - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$99

Non-stop • 60 min

BDL

Windsor Locks

BDL - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$99

Non-stop • 60 min

ALB

Windsor Locks

ALB - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$141

Non-stop • 60 min

BDL

Windsor Locks

BDL - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$148

Non-stop • 60 min

BTV

Windsor Locks

BTV - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$150

Non-stop • 60 min

ALB

Windsor Locks

ALB - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$166

Non-stop • 60 min

BTV

Windsor Locks

BTV - Windsor Locks • 2025-10-14 • 09:00

Unknown

60 min

MDW

Unknown City

$269

Non-stop • 60 min

Weather & Climate Information

Temperature

Chicago experiences a humid continental climate, with summer temperatures averaging 70-85°F (21-29°C) and winter lows often dropping to 20°F (-6°C) or below. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and precipitation is generally lower.

Rainfall

The best time to visit Chicago is during late spring (May to early June) or early fall (September to October) when temperatures are mild and the city is vibrant with outdoor festivals. These shoulder seasons also allow you to avoid the summer tourist crowds while enjoying iconic events like the Chicago Blues Festival and the Chicago Gourmet food festival.

Airlines at MDW

Book your journey from Windsor Locks to Chicago with leading airlines including Southwest Airlines, Delta Air Lines, Frontier Airlines, Allegiant Air. These carriers provide excellent connectivity and multiple daily options for convenient travel. The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Windsor Locks to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline, where iconic architecture meets vibrant lakeside beauty. Visitors can immerse themselves in rich history at the Art Institute, savor deep-dish pizza, and stroll along the bustling streets of Millennium Park, home to the famous Cloud Gate sculpture. With a dynamic arts scene, diverse neighborhoods, and world-class museums, Chicago offers an unforgettable blend of culture and culinary delights that beckon explorers to uncover its many treasures.

About Chicago

Embark on an exciting adventure from Windsor Locks to Chicago and discover a world of possibilities. This dynamic city offers a perfect mix of traditional charm and contemporary attractions. Time your visit during off-peak periods for maximum savings and comfort.

Airlines Flying from Windsor Locks to Chicago

Book your journey from Windsor Locks to Chicago with leading airlines including Southwest Airlines, Delta Air Lines, Frontier Airlines, Allegiant Air. These carriers provide excellent connectivity and multiple daily options for convenient travel. The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Windsor Locks to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional service.

Hotels in Chicago

Discover top-rated hotels near MDW Airport for your stay in Chicago. These accommodations offer excellent connectivity to MDW Airport and provide modern amenities for business and leisure travelers. Book early to secure the best rates and availability.

Hotel

Category: Standard

Comfortable accommodations with modern amenities.

Location: Near airport

Hotel ID:

About Chicago

Embark on an exciting adventure from Windsor Locks to Chicago and discover a world of possibilities. This dynamic city offers a perfect mix of traditional charm and contemporary attractions. Time your visit during off-peak periods for maximum savings and comfort.

Places to Visit in Chicago

Chicago, the Windy City, captivates with its stunning skyline, where iconic architecture meets vibrant lakeside beauty. Visitors can immerse themselves in rich history at the Art Institute, savor deep-dish pizza, and stroll along the bustling streets of Millennium Park, home to the famous Cloud Gate sculpture. With a dynamic arts scene, diverse neighborhoods, and world-class museums, Chicago offers an unforgettable blend of culture and culinary delights that beckon explorers to uncover its many treasures.

Hotels in Chicago

Discover top-rated hotels near MDW Airport for your stay in Chicago. These accommodations offer excellent connectivity to MDW Airport and provide modern amenities for business and leisure travelers. Book early to secure the best rates and availability.

Hotel

Category: Standard

Comfortable accommodations with modern amenities.

Location: Near airport

Hotel ID:

Airlines Flying from Windsor Locks to Chicago

Book your journey from Windsor Locks to Chicago with leading airlines including Southwest Airlines, Delta Air Lines, Frontier Airlines, Allegiant Air. These carriers provide excellent connectivity and multiple daily options for convenient travel. The typical flight time is about 10-15 hours, with most flights featuring one stopover for better pricing and route optimization. When traveling from Windsor Locks to Chicago, these airlines ensure a smooth and comfortable experience with their modern fleet and professional 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 Southwest Airlines, Delta Air Lines, 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 MDW Airport?

There are several hotels near MDW 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.

Flights from Windsor Locks to Chicago from $55

Explore flight options from Windsor Locks to Chicago with competitive pricing starting from $365.

Windsor Locks

→

Chicago

Cheap flight deals from Windsor Locks to Chicago

Average price start from:

$237

One-way from:

$55

Cheapest day:

Wednesday

Cheapest In:

January

Find flight deals from Windsor Locks to Chicago

Cheapest flights from Windsor Locks to Chicago

BDL

MDW

$55

BTV

MDW

$85

ALB

MDW

$89

BDL

MDW

$89

ALB

MDW

$99

BDL

MDW

$99

ALB

MDW

$141

BDL

MDW

$148

BTV

MDW

$150

ALB

MDW

$166

BTV

MDW

$269

Weather & Climate Information

Temperature

Rainfall

Airlines at MDW

Places to Visit in Chicago

About Chicago

Airlines Flying from Windsor Locks to Chicago

Hotels in Chicago

Hotel

About Chicago

Places to Visit in Chicago

Hotels in Chicago

Hotel

Airlines Flying from Windsor Locks to Chicago

Frequently Asked Questions

How much does it cost to fly from Windsor Locks to Chicago?

What's the flight duration from Windsor Locks to Chicago?

What airlines serve the Windsor Locks to Chicago route?

When should I book my flight for the best price?

Where can I stay near MDW Airport?

What makes Chicago worth visiting?

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