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Find cheap flights from Chicago to Glenwood Springs from $244

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 6/10. 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.
1 adult
0 bags
Sat 6/1
Sat 6/8

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Good to know

Low season

August

High season

March

Cheapest flight

$244
Best time to beat the crowds with an average 20% drop 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 3h 04m.

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

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

  • 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 $244. American Airlines offered a round-trip connection from $370 and United Airlines from $420.

See more FAQs

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 27 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 August, September and October. The cheapest month to fly is August.
See more tips

Top airlines flying from 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 11142 reviews
8.1Crew
7.2Comfort
7.7Boarding
6.7Food
7.1Entertainment
Airline reviews

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

8.0 ExcellentAnonymous, Apr 2024ORD - PHX
Read more about United Airlines reviews

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Book cheap flights from Chicago to Glenwood Springs

Recent round-trip flight deals

6/13Thu
1 stopAmerican Airlines
5h 48mORD-EGE
6/14Fri
1 stopAmerican Airlines
6h 59mEGE-ORD
$370
9/14Sat
1 stopAmerican Airlines
6h 31mORD-EGE
9/18Wed
1 stopAmerican Airlines
7h 41mEGE-ORD
$400
10/19Sat
1 stopUnited Airlines
4h 40mORD-EGE
10/26Sat
1 stopUnited Airlines
4h 38mEGE-ORD
$420
5/28Tue
2 stopsAmerican Airlines
16h 18mORD-EGE
5/30Thu
1 stopAmerican Airlines
7h 02mEGE-ORD
$444
5/28Tue
1 stopAmerican Airlines
6h 38mORD-EGE
5/30Thu
1 stopAmerican Airlines
7h 02mEGE-ORD
$454
9/14Sat
2 stopsAmerican Airlines
14h 25mORD-EGE
9/18Wed
1 stopAmerican Airlines
5h 59mEGE-ORD
$470
6/21Fri
1 stopAmerican Airlines
7h 59mORD-EGE
6/23Sun
1 stopAmerican Airlines
7h 54mEGE-ORD
$474
6/21Fri
nonstopUnited Airlines
3h 04mORD-EGE
6/23Sun
nonstopUnited Airlines
2h 44mEGE-ORD
$481
6/21Fri
1 stopUnited Airlines
6h 46mORD-EGE
6/23Sun
nonstopUnited Airlines
2h 44mEGE-ORD
$490
10/19Sat
2 stopsAmerican Airlines
16h 20mORD-EGE
10/26Sat
1 stopAmerican Airlines
7h 16mEGE-ORD
$519

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Recent one-way flight deals

6/10Mon
1 stopAmerican Airlines
7h 59mORD-EGE
$244
6/10Mon
2 stopsUnited Airlines
21h 55mORD-EGE
$328

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Flights to Glenwood Springs