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Glenwood Springs

$221+ Cheap flights from Chicago (CHI) to Glenwood Springs, CO

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MTJ
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Glenwood Springs are usually found in April or January, booked 31 days in advance, depart on a Wednesday or Friday and return on a Tuesday

Cheap flight deals from Chicago to Glenwood Springs

Keep the following information in mind while searching for Chicago to Glenwood Springs flight deals. Data was last updated September 22, 2025.

Round-trip from

$249
(United Airlines)

One-way from

$221
(United Airlines)

Popular in

July

Cheapest in

April

Average price

$548
From Chicago (CHI) to Glenwood Springs
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One-way flight from Chicago (CHI) to Glenwood Springs
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Highest demand for flights based on searches. 8% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Glenwood Springs

Cheapest flights from Chicago to Glenwood Springs
Explore the most affordable flight options available from Chicago to Glenwood Springs. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2025.

This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:55 amORD - EGE
Nonstop2h 56mUnited Airlines
Sat 12/131:20 pmEGE - ORD
Nonstop2h 48mUnited Airlines
Deal found 9/20$249
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2310:45 amORD - EGE
Nonstop3h 06mAmerican Airlines
Wed 12/313:50 pmEGE - ORD
1 stop7h 26mAmerican Airlines
Deal found 9/21$259
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1911:46 amORD - EGE
1 stop8h 25mAmerican Airlines
Mon 11/248:00 amEGE - ORD
1 stop6h 32mAmerican Airlines
Deal found 9/21$269
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/184:20 pmORD - EGE
Nonstop3h 01mUnited Airlines
Mon 12/2212:20 pmEGE - ORD
Nonstop2h 55mUnited Airlines
Deal found 9/21$273
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:06 amORD - EGE
1 stop9h 10mAmerican Airlines
Mon 12/2212:01 pmEGE - ORD
Nonstop3h 00mAmerican Airlines
Deal found 9/22$299
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:51 pmORD - EGE
1 stop7h 41mUnited Airlines
Tue 12/163:20 pmEGE - ORD
1 stop7h 39mUnited Airlines
Deal found 9/21$321
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:40 pmORD - EGE
1 stop6h 52mUnited Airlines
Sat 12/131:20 pmEGE - ORD
Nonstop2h 48mUnited Airlines
Deal found 9/20$335
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:55 amORD - EGE
Nonstop2h 56mUnited Airlines
Mon 12/153:20 pmEGE - ORD
1 stop7h 39mUnited Airlines
Deal found 9/20$339

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Glenwood Springs that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 22, 2025.
Use the filters below to find and compare flights from Chicago to Glenwood Springs that are best for you.

Fly from

Chicago

Fly to

Glenwood Springs

Route

Depart

Return

Price

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/6

2:40 pm-8:32 pm

1 stop6h 52m

Vail Eagle County

Sat 12/13

1:28 pm-7:44 pm

1 stop5h 16m

$264

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 12/18

4:20 pm-6:21 pm

Nonstop3h 01m

Vail Eagle County

Mon 12/22

3:30 pm-11:00 pm

1 stop6h 30m

$283

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Thu 12/18

8:16 am-3:16 pm

1 stop8h 00m

Vail Eagle County

Mon 12/22

12:01 pm-4:01 pm

Nonstop3h 00m

$299

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/13

1:51 pm-8:32 pm

1 stop7h 41m

Vail Eagle County

Tue 12/16

3:20 pm-11:59 pm

1 stop7h 39m

$321

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Tue 12/9

2:40 pm-8:32 pm

1 stop6h 52m

Vail Eagle County

Sat 12/13

1:20 pm-5:08 pm

Nonstop2h 48m

$335

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/6

8:55 am-10:51 am

Nonstop2h 56m

Vail Eagle County

Fri 12/12

1:28 pm-7:44 pm

1 stop5h 16m

$339

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/6

8:55 am-10:51 am

Nonstop2h 56m

Vail Eagle County

Mon 12/15

3:20 pm-11:59 pm

1 stop7h 39m

$339

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Mon 12/8

1:51 pm-8:32 pm

1 stop7h 41m

Vail Eagle County

Sat 12/13

1:20 pm-5:08 pm

Nonstop2h 48m

$339

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/6

8:55 am-10:51 am

Nonstop2h 56m

Vail Eagle County

Tue 12/16

1:30 pm-9:08 pm

1 stop6h 38m

$339

ChicagoVail

ORD - EGE

ORDEGE

Chicago O'Hare Intl

Sat 12/6

2:40 pm-8:32 pm

1 stop6h 52m

Vail Eagle County

Wed 12/10

1:30 pm-7:44 pm

1 stop5h 14m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/20

Showing 1-10 of 20 results
1
2

Best time to book a flight from Chicago to Glenwood Springs

Have a flexible travel schedule? Discover the best time to fly to Glenwood Springs from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Glenwood Springs

How far ahead should I book a flight from Chicago to Glenwood Springs?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Glenwood Springs. Price data was last updated on September 19, 2025.

Booking 30 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Glenwood Springs. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Glenwood Springs?

Currently, October is the cheapest month in which you can book a flight from Chicago to Glenwood Springs (average of $371). Flying from Chicago to Glenwood Springs in March is currently the most expensive (average of $539). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to GL9?

Find hourly flight availability from Chicago to Glenwood Springs. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 22, 2025.

When flying from Chicago to Glenwood Springs, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Glenwood Springs?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Glenwood Springs. Price data was last updated on September 29, 2024.

Travelers seeking maximum savings on their Chicago to Glenwood Springs flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Glenwood Springs

Get insights into the airlines that provide service to Glenwood Springs. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Glenwood Springs. Reviews last updated September 22, 2025.
Get a feel of what it's like to fly with United Airlines, American Airlines, and Frontier from Chicago to Glenwood Springs by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,922 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
United Airlines
7.4
Good
8,922 reviews
United Airlines
7.4
Good
8,922 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,922 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.
Frontier
5.8
Fair
3,166 reviews
United Airlines
7.4
Good
8,922 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Julia,Sep 2025

BUF - DEN

The staff were amazing, from check in to boarding and on the flight. The range of entertainment options were really good as well.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Glenwood Springs. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Glenwood Springs?

    Airlines like United Airlines and American Airlines fly from Chicago to Glenwood Springs in about 6h 52m. The time it takes to get you to your destination can typically vary by up to 1h 08m. Airlines will cover a distance of 1004 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest flights from Chicago to Glenwood Springs?

    Looking for the cheapest flight from Chicago to Glenwood Springs? While on average our users pay $501, our data indicates the cheapest price to be $309. The most popular route (Chicago O'Hare Intl - Vail Eagle County), is priced around $248.

  • Can I find deals for flights from Chicago to Glenwood Springs that include hotel bookings?

    Yes. In addition to deals on Chicago to Glenwood Springs flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Glenwood Springs?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Glenwood Springs.

  • Can I find deals for business class flights from Chicago to Glenwood Springs?

    Yes. Cheapflights offers flight deals from Chicago to Glenwood Springs by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Glenwood Springs?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Glenwood Springs (average of $371). Flying from Chicago to Glenwood Springs in March is currently the most expensive (average of $539). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Glenwood Springs

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Glenwood Springs

Discover the top 3 airlines that operate flights from Chicago to Glenwood Springs. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$239Average$486FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$299Average$560FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$318Average$398FlexibilityNo cancel feeOn-time63%

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