$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 4/12. 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
$329
Overall average: $483
American Airlines
Thu 4/2Sun 4/5
ORD - EGE • Non-stop
Cheapest one-way
$208
Typical prices: $346-$491
United Airlines
Sun 4/12
ORD - EGE • 1 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

Thu, Apr 2 - Sun, Apr 5
American Airlines Logo
10:34 am - 12:40 pm
ORD
-
EGE
3h 06mnonstop
American Airlines Logo
12:05 pm - 3:53 pm
EGE
-
ORD
2h 48mnonstop
$329American Airlines
Thu, Apr 2 - Sun, Apr 5
American Airlines Logo
11:45 am - 7:22 pm
ORD
-
EGE
8h 37m
1 stop
American Airlines Logo
10:48 am - 2:36 pm
EGE
-
ORD
2h 48mnonstop
$339American Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
10:34 am - 12:40 pm
ORD
-
EGE
3h 06mnonstop
American Airlines Logo
10:48 am - 2:36 pm
EGE
-
ORD
2h 48mnonstop
$344American Airlines
Wed, Apr 29 - Wed, May 6
American Airlines Logo
11:43 am - 7:09 pm
ORD
-
EGE
8h 26m
1 stop
American Airlines Logo
8:00 am - 3:18 pm
EGE
-
ORD
6h 18m
1 stop
$346American Airlines
Sat, Apr 18 - Wed, Apr 22
United Airlines Logo
4:10 pm - 8:22 pm
ORD
-
EGE
5h 12m
1 stop
United Airlines Logo
1:38 pm - 9:20 pm
EGE
-
ORD
6h 42m
1 stop
$349United Airlines
Mon, Mar 30 - Mon, Apr 6
American Airlines Logo
5:00 am - 11:54 am
ORD
-
EGE
7h 54m
1 stop
American Airlines Logo
10:48 am - 2:36 pm
EGE
-
ORD
2h 48mnonstop
$354American Airlines
Fri, Mar 27 - Tue, Mar 31
United Airlines Logo
9:10 am - 11:20 am
ORD
-
EGE
3h 10mnonstop
United Airlines Logo
12:32 pm - 4:30 pm
EGE
-
ORD
2h 58mnonstop
$359United Airlines
Fri, Jun 19 - Mon, Jun 22
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
United Airlines Logo
3:25 pm - 11:19 pm
EGE
-
ORD
6h 54m
1 stop
$360United Airlines
Tue, Mar 31 - Sat, Apr 4
American Airlines Logo
5:00 am - 11:02 am
ORD
-
EGE
7h 02m
1 stop
American Airlines Logo
10:48 am - 2:36 pm
EGE
-
ORD
2h 48mnonstop
$369American Airlines
Thu, Mar 26 - Mon, Mar 30
American Airlines Logo
6:10 am - 11:50 am
ORD
-
EGE
6h 40m
1 stop
American Airlines Logo
4:17 pm - 12:51 am
EGE
-
ORD
7h 34m
1 stop
$379American Airlines
Useful Info

Good to know

Low seasonMay
Cheapest flight$208
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 18% 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 01m.

  • How many flights are there between Chicago and Glenwood Springs?

    6 direct flights run between Chicago and Glenwood Springs on a daily basis. On average, there are about 42 departures each week.

  • 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 $289.

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 9427 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

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

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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

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