$204 Find Cheap Flights from Chicago to Glenwood Springs - Compare and Save

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 1/30. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$398
Typical prices: $308-$309
American Airlines
Sun 9/13Wed 9/16
ORD - EGE • 1 stop
Cheapest non-stop
$499
United Airlines
Sat 12/5Sat 12/12
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.
FAQs
FAQs
FAQs
FAQs
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Glenwood Springs!
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, Sep 13 - Wed, Sep 16
American Airlines Logo
6:00 am - 12:17 pm
ORD
-
EGE
7h 17m
1 stop
American Airlines Logo
12:58 pm - 6:29 am
EGE
-
ORD
16h 31m
2 stops
$398American Airlines
Sun, Sep 13 - Wed, Sep 16
American Airlines Logo
6:00 am - 12:17 pm
ORD
-
EGE
7h 17m
1 stop
American Airlines Logo
12:58 pm - 9:09 pm
EGE
-
ORD
7h 11m
1 stop
$425American Airlines
Tue, Sep 8 - Fri, Sep 11
American Airlines Logo
6:00 am - 1:28 pm
ORD
-
EGE
8h 28m
1 stop
American Airlines Logo
12:58 pm - 9:09 pm
EGE
-
ORD
7h 11m
1 stop
$425American Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
12:11 pm - 7:12 pm
ORD
-
EGE
8h 01m
1 stop
American Airlines Logo
7:44 am - 4:16 pm
EGE
-
ORD
7h 32m
1 stop
$425American Airlines
Tue, Nov 3 - Tue, Nov 10
United Airlines Logo
2:30 pm - 8:31 pm
ORD
-
EGE
7h 01m
1 stop
United Airlines Logo
1:31 pm - 8:05 pm
EGE
-
ORD
5h 34m
1 stop
$485United Airlines
Fri, Sep 18 - Fri, Sep 25
United Airlines Logo
4:00 pm - 6:02 pm
ORD
-
EGE
3h 02mnonstop
United Airlines Logo
3:31 pm - 9:52 pm
EGE
-
ORD
5h 21m
1 stop
$492United Airlines
Thu, Dec 24 - Thu, Dec 31
United Airlines Logo
4:20 pm - 6:25 pm
ORD
-
EGE
3h 05mnonstop
United Airlines Logo
3:28 pm - 11:58 pm
EGE
-
ORD
7h 30m
1 stop
$492United Airlines
Sat, Dec 26 - Wed, Dec 30
Alaska Airlines Logo
6:57 pm - 3:48 pm
ORD
-
EGE
21h 51m
1 stop
Alaska Airlines Logo
4:28 pm - 1:19 pm
EGE
-
ORD
19h 51m
2 stops
$964Alaska Airlines
Sat, Dec 26 - Wed, Dec 30
Alaska Airlines Logo
6:57 pm - 3:48 pm
ORD
-
EGE
21h 51m
1 stop
Alaska Airlines Logo
6:10 pm - 6:54 pm
EGE
-
ORD
23h 44m
1 stop
$1,001Alaska Airlines
Wed, Dec 23 - Sun, Dec 27
Delta Logo
6:00 am - 10:50 am
ORD
-
EGE
5h 50m
1 stop
Delta Logo
11:30 am - 11:50 pm
EGE
-
ORD
11h 20m
2 stops
$1,003Delta
Useful Info

Good to know

Low season

October

Cheapest flight

$204
Best time to beat the crowds with an average 53% drop in price.
Most popular time to fly and prices are also 25% 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 02m.

  • 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 October.

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 10059 reviews
8.1Crew
6.6Food
7.7Boarding
7.3Comfort
7.1Entertainment
Airline reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

8.0 ExcellentArmedrest, Jul 2026
ORD - PAH
Read more United Airlines reviews

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

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

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

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

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

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