$272 Find Cheap Flights from Chicago to Glenwood Springs

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Glenwood Springs departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flight Deals from Chicago to Glenwood Springs (CHI-EGE)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Glenwood Springs that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Glenwood Springs

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Glenwood Springs.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
5:00 am - 9:47 amORD-EGE
5h 47m1 stop
American Airlines Logo
2:39 pm - 11:43 pmEGE-ORD
8h 04m1 stop
$309American Airlines
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Wed, Jun 18 - Wed, Jun 25
American Airlines Logo
1:58 pm - 6:52 pmORD-EGE
5h 54m1 stop
American Airlines Logo
8:00 am - 3:29 pmEGE-ORD
6h 29m1 stop
$324American Airlines
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Fri, May 16 - Wed, May 21
American Airlines Logo
11:55 am - 6:40 pmORD-EGE
7h 45m1 stop
American Airlines Logo
10:27 am - 6:35 pmEGE-ORD
7h 08m1 stop
$364American Airlines
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Thu, Jun 5 - Mon, Jun 9
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
United Airlines Logo
8:50 am - 12:38 pmEGE-ORD
2h 48mnonstop
$369United Airlines
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Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
7:10 am - 12:38 pmORD-EGE
6h 28m1 stop
United Airlines Logo
8:50 am - 12:38 pmEGE-ORD
2h 48mnonstop
$379United Airlines
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Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
2:33 pm - 8:01 pmORD-EGE
6h 28m1 stop
United Airlines Logo
1:45 pm - 8:00 pmEGE-ORD
5h 15m1 stop
$389United Airlines
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Sat, May 24 - Sun, May 25
United Airlines Logo
2:33 pm - 8:01 pmORD-EGE
6h 28m1 stop
United Airlines Logo
8:50 am - 12:38 pmEGE-ORD
2h 48mnonstop
$394United Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
United Airlines Logo
7:25 am - 9:41 amEGE-ORD
25h 16m1 stop
$404United Airlines
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Fri, Jul 4 - Tue, Jul 8
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
United Airlines Logo
7:25 am - 11:25 amEGE-ORD
27h 00m1 stop
$413United Airlines
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Fri, Jul 4 - Fri, Jul 11
United Airlines Logo
7:10 am - 12:37 pmORD-EGE
6h 27m1 stop
United Airlines Logo
7:25 am - 12:30 amEGE-ORD
16h 05m1 stop
$414United Airlines
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Tue, Jul 1 - Tue, Jul 8
Useful Info

Good to know

Low seasonMay
High seasonFebruary
Cheapest flight$272
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Chicago to Vail

When to book flights from Chicago to Glenwood Springs

Are your dates flexible? Find out the best times to travel from Chicago to Glenwood Springs based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Glenwood Springs

  • Which airports will I be using when flying from Chicago to Glenwood Springs?

    When flying out of Chicago you’ll be using Chicago O'Hare Intl. Glenwood Springs does not have its own airport so you’ll be flying into nearby Vail Eagle County airport, which is 22.5 mi away.

  • How long does a flight from Chicago to Glenwood Springs take?

    Direct flights cover the 1,018 miles separating Chicago and Glenwood Springs in about 2h 53m.

  • What’s the cheapest day of the week to fly between Chicago and Glenwood Springs?

    Consider leaving on a Wednesday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

  • How does KAYAK find such low prices on flights from Chicago to Glenwood Springs?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Glenwood Springs.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Glenwood Springs?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Glenwood Springs from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Glenwood Springs?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Glenwood Springs with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Glenwood Springs?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Glenwood Springs from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Glenwood Springs?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Glenwood Springs found on KAYAK was with American Airlines for $272. American Airlines offered a round-trip connection from $309 and United Airlines from $369.

Top tips for finding cheap flights from Chicago to Glenwood Springs

  • There is no airport in Glenwood Springs. Instead, you’ll be flying into Vail Eagle County Airport when flying between Chicago and Glenwood Springs.
  • The cheapest flight from Chicago to Glenwood Springs was found 74 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be June, July and August. The cheapest month to fly is April.

Top 3 airlines serving Chicago to Glenwood Springs

Need help choosing which airline to fly with from Chicago to Glenwood Springs? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8696 reviews
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

A bit rush for transit. Food and entertainment are not available

8.0 ExcellentAnonymous, Apr 2025ORD - SFO
Read more United Airlines reviews

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

The plane failed preflight inspection, so we sat there for 90 mins while they tried to fix it. Ultimately, everything was remedied and we made our connecting flight; instead of a 2 hour layover at the airport, we spent it waiting on the plane.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Delayed each time on a round trip with no significant weather interference. Updates to flight times came after the fact. 30 min behind in boarding and board and phone still show an on time departure. Some mysterious extra 300 miles that came so surprising they had to fuel while we were already on board?

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

Stuck in Phoenix for two days, not even a hotel voucher offered.

Every day about it was very different all the boarding pass where all wrong l miss flight no refund all crazy

Flight got delayed for 3.5 hours, and for the first hour after the departure time there was no update from the gate folks...

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

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