Flights from Colorado Springs to Chicago from $138
Explore flight options from Colorado Springs to Chicago with competitive pricing starting from $350.
Colorado Springs
COS
→
Chicago
ORD
11/24/2025 – 12/01/2025
Cheap flight deals from Colorado Springs to Chicago
Average price start from:
i
$265
Round-trip flights from Colorado Springs to Chicago starting at $265. Book now for the best deals!
One-way from:
i
$138
One-way flights from Colorado Springs to Chicago starting at $138. Great for flexible travel!
Cheapest day:
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Wednesday
Wednesday is the cheapest day to fly from Colorado Springs to Chicago. Save more by booking on this day!
Cheapest In:
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$28
Apr 2025
Apr 2025 is the cheapest month to fly from Colorado Springs to Chicago with prices starting at $28.
Find flight deals from Colorado Springs to Chicago
Cheapest flights from Colorado Springs to Chicago
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Explore the cheapest oneway flights from Colorado Springs to Chicago spotted daily.
COS
Colorado Springs
COS - Colorado Springs • 2025-11-24 • 09:00
Unknown
60 min
ORD
Unknown City
$138
Non-stop • 60 min
COS
Colorado Springs
COS - Colorado Springs • 2025-11-24 • 09:00
Unknown
60 min
ORD
Unknown City
$148
Non-stop • 60 min
COS
Colorado Springs
COS - Colorado Springs • 2025-11-24 • 09:00
Unknown
60 min
ORD
Unknown City
$156
Non-stop • 60 min
COS
Colorado Springs
COS - Colorado Springs • 2025-11-24 • 09:00
Unknown
60 min
ORD
Unknown City
$168
Non-stop • 60 min
COS
Colorado Springs
COS - Colorado Springs • 2025-11-24 • 09:00
Unknown
60 min
ORD
Unknown City
$216
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
Optimal pricing available on Wednesday for flights to Chicago.
Monthly Price Trends
Save the most on flights from Colorado Springs to Chicago in September.
Weather & Climate Information
Temperature
Chicago experiences four distinct seasons, with summer temperatures averaging 70-85°F (21-29°C) and winter lows dropping to 15°F (-9°C). The best times for comfortable travel are late spring (May-June) and early fall (September-October), when temperatures are mild and humidity is lower, making outdoor activities more enjoyable.
Rainfall
The best time to visit Chicago is during late spring (May) or early fall (September), when the weather is mild and pleasant. During these months, you can enjoy vibrant local events like the Chicago Blues Festival and the Chicago Gourmet, while avoiding the summer tourist crowds.
Airlines at Chicago
Discover excellent flight options from Colorado Springs to Chicago with top airlines including United Airlines, Delta Air Lines, American Airlines, Southwest Airlines. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Colorado Springs to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Places to Visit in Chicago
Chicago, the Windy City, beckons with its stunning skyline and vibrant arts scene, where the echoes of jazz and blues create a soulful soundtrack. Explore the historic architecture along the Chicago River, marvel at the iconic Millennium Park's Cloud Gate, and immerse yourself in the rich tapestry of culture at world-class museums like the Art Institute. Visitors can savor deep-dish pizza, stroll through bustling markets, and witness the city’s dynamic spirit, making every moment an unforgettable adventure in this Midwestern gem.
About Chicago
Discover the beauty of Chicago when flying from Colorado Springs. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.
Airlines Flying from Colorado Springs to Chicago
Discover excellent flight options from Colorado Springs to Chicago with top airlines including United Airlines, Delta Air Lines, American Airlines, Southwest Airlines. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Colorado Springs to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Hotels in Chicago
For accommodations near Chicago Airport (ORD), consider booking hotels in the city center or near the airport. Many hotels offer shuttle services to and from the airport for convenient travel.
About Chicago
Discover the beauty of Chicago when flying from Colorado Springs. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.
Places to Visit in Chicago
Chicago, the Windy City, beckons with its stunning skyline and vibrant arts scene, where the echoes of jazz and blues create a soulful soundtrack. Explore the historic architecture along the Chicago River, marvel at the iconic Millennium Park's Cloud Gate, and immerse yourself in the rich tapestry of culture at world-class museums like the Art Institute. Visitors can savor deep-dish pizza, stroll through bustling markets, and witness the city’s dynamic spirit, making every moment an unforgettable adventure in this Midwestern gem.
Hotels in Chicago
For accommodations near Chicago Airport (ORD), consider booking hotels in the city center or near the airport. Many hotels offer shuttle services to and from the airport for convenient travel.
Airlines Flying from Colorado Springs to Chicago
Discover excellent flight options from Colorado Springs to Chicago with top airlines including United Airlines, Delta Air Lines, American Airlines, Southwest Airlines. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Colorado Springs to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Frequently Asked Questions
What's the best deal for flights from Colorado Springs to Chicago?
The lowest fare available is $138. Maximize savings by booking during September and selecting Wednesday flights.
How many hours does it take to fly from Colorado Springs to Chicago?
Flight duration typically ranges around 10-15 hours, with most flights including one stopover for optimal route efficiency.
Which carriers fly between Colorado Springs and Chicago?
Major airlines serving this route include United Airlines, Delta Air Lines, American Airlines. Each offers different schedules and amenities to suit various travel preferences.
What's the ideal booking window for this route?
Book 2-3 months in advance for the best prices. Traveling during September can provide additional savings opportunities.
Are there convenient hotels near ORD Airport?
Yes, ORD Airport is surrounded by hotels offering shuttle services and modern amenities for travelers.
Why should I visit Chicago?
Chicago offers an incredible mix of cultural experiences and modern attractions. Plan your visit during pleasant weather months for the most enjoyable experience.
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