ORD - EGE

$221 Find Cheap Flights from Chicago to Vail

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 Vail departing on 12/23. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Vail

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Vail, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Vail, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chicago to Vail (ORD-EGE)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Vail 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 Vail

Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
9:45 am - 11:52 amORD-EGE
3h 07mnonstop
American Airlines Logo
1:03 pm - 4:55 pmEGE-ORD
2h 52mnonstop
$249American Airlines
Find Deal
Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
9:45 am - 11:52 amORD-EGE
3h 07mnonstop
American Airlines Logo
8:20 am - 3:26 pmEGE-ORD
6h 06m1 stop
$259American Airlines
Find Deal
Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
11:47 am - 6:04 pmORD-EGE
7h 17m1 stop
American Airlines Logo
2:32 pm - 11:51 pmEGE-ORD
8h 19m1 stop
$269American Airlines
Find Deal
Sun, Jan 11 - Sat, Jan 17
Delta Logo
5:50 am - 1:55 pmORD-EGE
9h 05m1 stop
Delta Logo
11:31 am - 11:54 pmEGE-ORD
11h 23m2 stops
$274Delta
Find Deal
Fri, Jan 30 - Mon, Feb 2
American Airlines Logo
9:45 am - 11:52 amORD-EGE
3h 07mnonstop
American Airlines Logo
1:03 pm - 4:55 pmEGE-ORD
2h 52mnonstop
$289American Airlines
Find Deal
Thu, Dec 18 - Sun, Dec 21
United Airlines Logo
9:00 am - 11:04 amORD-EGE
3h 04mnonstop
United Airlines Logo
8:25 am - 12:29 pmEGE-ORD
3h 04mnonstop
$292United Airlines
Find Deal
Thu, Dec 18 - Mon, Dec 22
United Airlines Logo
9:00 am - 11:04 amORD-EGE
3h 04mnonstop
United Airlines Logo
3:30 pm - 11:59 pmEGE-ORD
7h 29m1 stop
$302United Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
United Airlines Logo
1:55 pm - 8:31 pmORD-EGE
7h 36m1 stop
United Airlines Logo
1:30 pm - 8:58 pmEGE-ORD
6h 28m1 stop
$312United Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
8:47 am - 12:24 pmORD-EGE
4h 37m1 stop
United Airlines Logo
1:30 pm - 8:58 pmEGE-ORD
6h 28m1 stop
$329United Airlines
Find Deal
Mon, Jan 5 - Fri, Jan 9
Delta Logo
7:10 am - 1:55 pmORD-EGE
7h 45m1 stop
Delta Logo
2:56 pm - 11:54 pmEGE-ORD
7h 58m1 stop
$385Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Choose Main Cabin Extra on American for early boarding.
Use Priority Boarding on United for carry-on space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from $249 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 22% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$249
Overall average: $499
American Airlines
Sun 1/11Sat 1/17
ORD - EGE • Non-stop
Cheapest one-way
$221
Typical prices: $307-1576
American Airlines
Tue 12/23
ORD - EGE • Non-stop
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 Vail!
Expert advice

Expert advice for your flight from Chicago to Vail

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

Purchase Priority Boarding to ensure overhead bin space for your carry-on.


Check United's Wi-Fi coverage map before purchasing inflight Wi-Fi for better connectivity.

American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on medium-haul flights.


Download the American Airlines app for access to inflight entertainment on your device.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Vail flights

Get data-powered insights and trends into flights from Chicago to Vail to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Vail?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Vail clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Vail on a Wednesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Vail?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Vail, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Vail is October, where tickets cost $392 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $614 and $593 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Vail?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Vail, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Vail, you should book around 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$221
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago to Vail

When to book flights from Chicago to Vail

Are your dates flexible? Find out the best times to travel from Chicago to Vail based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Vail flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Vail?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Vail was $221 for a one-way ticket and $249 for a round-trip.

  • Do I need a passport to fly between Chicago and Vail?

    A passport is not required to fly from Chicago to Vail.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Vail?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Vail flight route.

  • Which aircraft models fly most regularly from Chicago to Vail?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Chicago to Vail flight route.

  • Which airline alliances offer flights from Chicago to Vail?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Vail, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Vail, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Vail are United Airlines and American Airlines. With an average price for the route of $585 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $498 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Vail?

    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 Vail.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Vail?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Vail 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 Vail?

    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 Vail with an airline and back to Chicago with another airline. Booking your flights between Chicago and EGE can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Vail?

    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 Vail from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Vail

  • Looking for a cheap flight? 25% of our users found flights on this route for $268 or less round-trip.

Reviews of the top airlines flying from Chicago to Vail

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Vail. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Vail? 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 8924 reviews
7.1Entertainment
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

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

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Everything you need to know for your flight from Chicago to Vail

Information on your arrival and departure airports

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