Cheap Flight Deals From Colorado Springs (DEN) to Chicago (CHI) Starting at $44

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This Weekend's Flight Deals from Colorado Springs to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jun 11 - Tue, Jun 13
DEN
Denver Intl.
ORD
O'Hare Intl.
$268 Roundtrip, just found
$268
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Jun 11 from Denver Intl. to O'Hare Intl., returning Tue, Jun 13, priced at $268 just found
Sat, Jun 10 - Wed, Jun 21
DEN
Denver Intl.
MDW
Midway Intl.
$280 Roundtrip, found 7 hours ago
$280
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Jun 10 from Denver Intl. to Midway Intl., returning Wed, Jun 21, priced at $280 found 7 hours ago
Sat, Jun 10 - Thu, Jun 15
COS
Colorado Springs
ORD
O'Hare Intl.
$555 Roundtrip, found 5 hours ago
$555
Roundtrip
found 5 hours ago
Select United flight, departing Sat, Jun 10 from Colorado Springs to O'Hare Intl., returning Thu, Jun 15, priced at $555 found 5 hours ago
Sat, Jun 10 - Thu, Jun 15
COS
Colorado Springs
MDW
Midway Intl.
$601 Roundtrip, found 5 hours ago
$601
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Jun 10 from Colorado Springs to Midway Intl., returning Thu, Jun 15, priced at $601 found 5 hours ago

Airfares from $44 One Way, $146 Round Trip from Colorado Springs to Chicago

Prices starting at $146 for return flights and $44 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jul 18 - Wed, Aug 9
DEN
Denver
ORD
Chicago
$146 Roundtrip, found 14 hours ago
$146
Roundtrip
found 14 hours ago
Select United flight, departing Tue, Jul 18 from Denver to Chicago, returning Wed, Aug 9, priced at $146 found 14 hours ago
Wed, Aug 30 - Wed, Sep 13
DEN
Denver
ORD
Chicago
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 30 from Denver to Chicago, returning Wed, Sep 13, priced at $178 found 2 days ago
Tue, Jul 4 - Tue, Jul 11
COS
Colorado Springs
ORD
Chicago
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jul 4 from Colorado Springs to Chicago, returning Tue, Jul 11, priced at $183 found 1 day ago
Fri, Aug 18 - Tue, Aug 22
DEN
Denver
MDW
Chicago
$199 Roundtrip, found 21 hours ago
$199
Roundtrip
found 21 hours ago
Select Delta flight, departing Fri, Aug 18 from Denver to Chicago, returning Tue, Aug 22, priced at $199 found 21 hours ago
Wed, Jun 28 - Sat, Jul 8
DEN
Denver
ORD
Chicago
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jun 28 from Denver to Chicago, returning Sat, Jul 8, priced at $204 found 2 days ago

Chicago economy flight packages

Silversmith Hotel Chicago Downtown
4.0-star property

Silversmith Hotel Chicago Downtown

9.2/10 Wonderful! (1,304 reviews)

Jul 29 - Aug 4

6 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Denver (DEN)

Delta • Non-stop • Coach
Save 100% on your flightPrice was $1,393, price is now $1,038 per person
per person
Front desk staff friendly and helpful; ditto doorman and bartender. Had breakfast on Sunday at hotel restaurant and felt put off by younger server, as if he was enjoying being cute w us. Do you have any cream for the coffee? “Yes”. But we’d have to ask for some to come to the table

Reviewed on Apr 29, 2023

The Emily Hotel
4.0-star property

The Emily Hotel

8.8/10 Excellent! (332 reviews)

Jul 29 - Aug 4

6 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Denver (DEN)

Delta • Non-stop • Coach
Save 100% on your flightPrice was $1,370, price is now $1,026 per person
per person
Had a great stay at The Emily Hotel. The room was good sized and had a comfortable bed and working space. It's in a great location in the West Loop near tons of restaurants. I will definitely stay here again.

Reviewed on Jan 26, 2023

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.2/10 Wonderful! (1,288 reviews)

Jul 29 - Aug 4

6 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Denver (DEN)

Delta • Non-stop • Coach
Save 100% on your flightPrice was $1,463, price is now $1,143 per person
per person
The view from the room was great, and being able to walk inside from the hotel to the shops at the Navy Pier was easy.

Reviewed on Mar 31, 2023

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More About Flying To Chicago from Colorado Springs

Route Information for Flights from Colorado Springs to Chicago

Origin Airport IATA Code
DEN
Destination Airport IATA Code
CHI
Distance
886 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, LOT - Polish Airlines, Austrian, Aer Lingus, Emirates, SWISS, United Airlines, Turkish Airlines, Southwest Airlines, Finnair, SAS, Royal Jordanian, Iberia, Brussels Airlines, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival
3:15PM UTC
Latest Flight Arrival
6:38AM UTC
Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

Traveling from Colorado Springs to Chicago

When you want a change of pace from the snowy mountains of Colorado Springs, Chicago offers a lovely lakefront setting and a bustling urban center. With Orbitz.com, you can find flights from Colorado Springs to Chicago and enjoy a quick booking process.

Flying out of Colorado Springs

The Colorado Springs Airport is the biggest airport in the area. It sits about six miles outside of town, making it an easy drive from anywhere in the city. Driving is the easiest way to reach the airport, and parking is available for just $6 per day in the long-term lot. If you would prefer to take a taxi, any of the local taxi companies can get you to the airport in less than thirty minutes.

Things to Do in Chicago

Often called the “Second City,” Chicago has a thriving cultural scene and a diverse population. From traveling musical productions to exciting sporting events, the city has something for everyone. Don’t miss the Shedd Aquarium, the Navy Pier, or the extensive waterfront trails. When you fly into Chicago, you’ll land at either the Chicago Midway International Airport or the Chicago O’Hare International Airport. The Midway Airport is closer to the center of the city. You can take the train from either airport into the downtown area in less than an hour. Taxis and rental cars are also readily available. When you’re packing for your trip, be sure to include cold-weather gear for winter days and light, breathable layers for summer adventures. In December and January, temperatures frequently drop to 25°F and lower. Summer days average 80°F with high humidity.

Experience Chicago

With its remarkable natural surroundings and world-class performing arts, Chicago makes the perfect vacation spot. After you find flights from Colorado Springs to Chicago on Orbitz.com, you can take advantage of the special offers on local attractions and tours.

Frequently asked questions

Am I able to catch a flight from Colorado Springs to Chicago now?
Head to the Covid-19 Travel Advisor for the most comprehensive information on travel restrictions and quarantine when flying from Colorado Springs to Chicago.
Are there non-stop flights from Colorado Springs to Chicago?
You can travel directly from DIA airport to O’Hare Intl. Airport (ORD), so get set to kiss those annoying flight connections goodbye. Enjoy a hassle-free trip on one of the 4 carriers that’ll take you straight to your destination. Top options include:

  • United Airlines
  • Southwest Airlines
  • American Airlines
  • Frontier Airlines

What is the shortest flight from Colorado Springs to Chicago?
The quickest flight from COS to Chicago, IL (ORD-O’Hare Intl.) is 3 hours and 15 minutes. Slip a few things into your hand luggage to stop you from getting bored, like a magazine or a sketch pad.
What airlines fly from Colorado Springs to Chicago most frequently?
Here are the airlines with the most frequent flights between Colorado Springs and Chicago. Discover which one best meets your needs: United Airlines - (UA) with 273 flights every month Southwest Airlines - (WN) with 173 flights every month American Airlines - (AA) with 139 flights every month Frontier Airlines - (F9) with 30 flights every month
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.