$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 6/9. 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: $485-$379
American Airlines
mar. 6/23mar. 6/30
ORD - EGE • 1 stop
Cheapest non-stop
$540
United Airlines
ven. 6/5dim. 6/7
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

mar., juin 23 - mar., juin 30
American Airlines Logo
5:59 am - 1:31 pm
ORD
-
EGE
8h 32m
1 stop
American Airlines Logo
2:12 pm - 10:30 pm
EGE
-
ORD
7h 18m
1 stop
$415American Airlines
ven., juin 26 - mar., juin 30
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
United Airlines Logo
3:25 pm - 9:39 pm
EGE
-
ORD
5h 14m
1 stop
$442United Airlines
sam., juin 27 - mer., juil. 1
United Airlines Logo
8:40 am - 2:23 pm
ORD
-
EGE
6h 43m
1 stop
United Airlines Logo
3:25 pm - 9:39 pm
EGE
-
ORD
5h 14m
1 stop
$452United Airlines
ven., mai 29 - dim., juin 7
United Airlines Logo
8:40 am - 2:23 pm
ORD
-
EGE
6h 43m
1 stop
United Airlines Logo
8:00 am - 11:40 am
EGE
-
ORD
2h 40mnonstop
$459United Airlines
lun., mai 25 - jeu., mai 28
American Airlines Logo
6:00 am - 1:31 pm
ORD
-
EGE
8h 31m
1 stop
American Airlines Logo
2:12 pm - 11:37 pm
EGE
-
ORD
8h 25m
1 stop
$463American Airlines
sam., juin 13 - sam., juin 20
American Airlines Logo
1:25 pm - 7:04 pm
ORD
-
EGE
6h 39m
1 stop
American Airlines Logo
10:33 am - 7:28 pm
EGE
-
ORD
7h 55m
1 stop
$467American Airlines
ven., mai 22 - sam., mai 30
American Airlines Logo
8:19 am - 1:31 pm
ORD
-
EGE
6h 12m
1 stop
American Airlines Logo
2:12 pm - 11:37 pm
EGE
-
ORD
8h 25m
1 stop
$469American Airlines
ven., juin 5 - dim., juin 7
American Airlines Logo
11:40 am - 7:04 pm
ORD
-
EGE
8h 24m
1 stop
American Airlines Logo
7:50 am - 3:39 pm
EGE
-
ORD
6h 49m
1 stop
$471American Airlines
dim., août 23 - jeu., sept. 3
American Airlines Logo
5:00 am - 9:47 am
ORD
-
EGE
5h 47m
1 stop
American Airlines Logo
7:50 am - 3:54 pm
EGE
-
ORD
7h 04m
1 stop
$483American Airlines
jeu., mai 14 - jeu., mai 21
American Airlines Logo
11:43 am - 7:09 pm
ORD
-
EGE
8h 26m
1 stop
American Airlines Logo
7:50 am - 3:44 pm
EGE
-
ORD
6h 54m
1 stop
$484American Airlines
Useful Info

Good to know

Cheapest flight$208
Most popular time to fly and prices are also 4% 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 05m.

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

    Consider leaving on a Sunday and avoid Thursdays 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 72 hours, 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 September, October and November. 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 9677 reviews
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

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

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

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.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

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.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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