$208 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 8/30. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$415
Typical prices: $374-$517
American Airlines
Sun 8/23Thu 9/3
ORD - EGE • 1 stop
Cheapest non-stop
$469
United Airlines
Sat 8/15Sat 8/22
ORD - EGE • Non-stop
Arrival airport
You can't fly directly to Glenwood Springs. It is served by Vail (EGE), located 22.5 miles from Glenwood Springs.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Glenwood Springs

Sun, Aug 23 - Thu, Sep 3
American Airlines Logo
12:11 pm - 6:53 pm
ORD
-
EGE
7h 42m
1 stop
American Airlines Logo
2:08 pm - 11:30 pm
EGE
-
ORD
8h 22m
1 stop
$415American Airlines
Tue, Oct 20 - Sat, Oct 24
American Airlines Logo
10:00 pm - 12:03 pm
ORD
-
EGE
15h 03m
2 stops
American Airlines Logo
12:50 pm - 9:14 pm
EGE
-
ORD
7h 24m
1 stop
$448American Airlines
Tue, Oct 20 - Sat, Oct 24
American Airlines Logo
6:00 am - 12:03 pm
ORD
-
EGE
7h 03m
1 stop
American Airlines Logo
12:50 pm - 9:14 pm
EGE
-
ORD
7h 24m
1 stop
$452American Airlines
Tue, Oct 20 - Sat, Oct 24
American Airlines Logo
10:00 pm - 12:03 pm
ORD
-
EGE
15h 03m
2 stops
American Airlines Logo
12:50 pm - 9:14 pm
EGE
-
ORD
7h 24m
1 stop
$459American Airlines
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
7:00 am - 1:28 pm
ORD
-
EGE
7h 28m
1 stop
American Airlines Logo
2:08 pm - 9:16 pm
EGE
-
ORD
6h 08m
1 stop
$463American Airlines
Sat, Aug 15 - Sat, Aug 22
United Airlines Logo
4:00 pm - 6:02 pm
ORD
-
EGE
3h 02mnonstop
United Airlines Logo
8:00 am - 11:59 am
EGE
-
ORD
2h 59mnonstop
$469United Airlines
Wed, Jul 15 - Tue, Jul 21
American Airlines Logo
11:00 am - 6:50 pm
ORD
-
EGE
8h 50m
1 stop
American Airlines Logo
10:33 am - 7:44 pm
EGE
-
ORD
8h 11m
1 stop
$472American Airlines
Sat, Jul 11 - Sat, Jul 18
United Airlines Logo
8:00 am - 12:03 pm
ORD
-
EGE
5h 03m
1 stop
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
$479United Airlines
Sat, Aug 22 - Wed, Aug 26
United Airlines Logo
4:00 pm - 6:02 pm
ORD
-
EGE
3h 02mnonstop
United Airlines Logo
1:30 pm - 10:00 pm
EGE
-
ORD
7h 30m
1 stop
$480United Airlines
Wed, Sep 16 - Sun, Sep 20
United Airlines Logo
7:00 am - 12:24 pm
ORD
-
EGE
6h 24m
1 stop
United Airlines Logo
7:50 am - 11:48 am
EGE
-
ORD
2h 58mnonstop
$483United Airlines
Useful Info

Good to know

Cheapest flight$208
Most popular time to fly and prices are also 11% 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 Sunday and avoid Tuesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Sundays and the most expensive ones on Tuesdays.

  • 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 5 days, the cheapest one-way ticket between Chicago and Glenwood Springs found on KAYAK was with American Airlines for $158. American Airlines offered a round-trip connection from $259 and United Airlines from $287.

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.
  • High season is considered to be October, November and December. The cheapest month to fly is January.

Reviews of the 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 9860 reviews
7.7Boarding
7.1Entertainment
6.7Food
8.1Crew
7.3Comfort
Airline reviews

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

2.0 MediocreAnonymous, Jun 2026
ORD - BHM
Read more United Airlines reviews

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

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

Complete your trip to Glenwood Springs with a hotel stay or car rental