EGE - CHI

$221 Find Cheap Flights from Vail to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Vail to Chicago departing on 12/21. 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

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

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

Cheap Flights from Vail to Chicago (EGE-CHI)

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

Fri, Dec 26 - Wed, Dec 31
American Airlines Logo
12:01 pm - 4:01 pmEGE-ORD
3h 00mnonstop
American Airlines Logo
8:05 am - 9:54 amORD-EGE
2h 49mnonstop
$340American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
United Airlines Logo
1:25 pm - 9:08 pmEGE-ORD
6h 43m1 stop
United Airlines Logo
2:40 pm - 8:32 pmORD-EGE
6h 52m1 stop
$346United Airlines
Find Deal
Sat, Dec 27 - Wed, Dec 31
American Airlines Logo
10:34 am - 2:34 pmEGE-ORD
3h 00mnonstop
American Airlines Logo
10:45 am - 12:51 pmORD-EGE
3h 06mnonstop
$349American Airlines
Find Deal
Fri, Dec 26 - Wed, Dec 31
American Airlines Logo
12:01 pm - 4:01 pmEGE-ORD
3h 00mnonstop
American Airlines Logo
5:00 am - 10:49 amORD-EGE
6h 49m1 stop
$350American Airlines
Find Deal
Sat, Dec 27 - Wed, Dec 31
United Airlines Logo
7:01 am - 1:19 pmEGE-ORD
5h 18m1 stop
United Airlines Logo
4:20 pm - 6:21 pmORD-EGE
3h 01mnonstop
$359United Airlines
Find Deal
Fri, Dec 26 - Wed, Dec 31
American Airlines Logo
3:50 pm - 12:16 amEGE-ORD
7h 26m1 stop
American Airlines Logo
5:00 am - 10:49 amORD-EGE
6h 49m1 stop
$360American Airlines
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
2:56 pm - 9:46 pmEGE-MDW
5h 50m1 stop
Delta Logo
6:00 am - 1:55 pmMDW-EGE
8h 55m1 stop
$481Delta
Find Deal
Thu, Mar 5 - Mon, Mar 9
Delta Logo
2:56 pm - 9:46 pmEGE-MDW
5h 50m1 stop
Delta Logo
6:00 am - 1:55 pmMDW-EGE
8h 55m1 stop
$485Delta
Find Deal
Fri, Dec 26 - Wed, Dec 31
Alaska Airlines Logo
1:17 pm - 6:29 amEGE-ORD
16h 12m2 stops
Alaska Airlines Logo
8:39 am - 5:46 pmORD-EGE
10h 07m1 stop
$865Alaska Airlines
Find Deal
Fri, Dec 26 - Wed, Dec 31
Alaska Airlines Logo
1:17 pm - 6:29 amEGE-ORD
16h 12m2 stops
Alaska Airlines Logo
7:00 am - 12:38 pmORD-EGE
30h 38m2 stops
$890Alaska Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
American's Main Cabin Extra includes early boarding.
United's Economy Plus offers extra legroom for comfort.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from $340 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
EGE-ORD
Cheapest
EGE-ORD
Most popular
Insights
Insights
Insights
Insights
Cheapest round-trip
$340
Overall average: $529
American Airlines
Fri 12/26Wed 12/31
EGE - ORD • Non-stop
Cheapest one-way
$221
Typical prices: $236-$315
American Airlines
Sun 12/21
EGE - ORD • 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 Chicago!
Booking Insights

KAYAK's insights & trends for Vail to Chicago flights

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

What is the cheapest Vail to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Vail to Chicago costs $191 on the route between Vail (EGE) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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

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

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

Can I save money by flying with a layover from Vail to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $249, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Vail to Chicago

 
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

United offers Priority Boarding to avoid gate-checking carry-ons, ideal for quick boarding.


United's Economy Plus seats provide up to six inches more legroom than standard economy.

American Airlines

American Airlines' Main Cabin Extra offers early boarding and complimentary drinks.


American Airlines provides 20 minutes of free Wi-Fi by watching a short advertisement.

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

Good to know

Cheapest flight$221
Most popular time to fly and prices are also 12% lower on average.
Flight from Vail to Chicago

When to book flights from Vail to Chicago

Are your dates flexible? Find out the best times to travel from Vail to Chicago 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 flights from Vail to Chicago

  • What is the cheapest flight from Vail to Chicago?

    In the last 3 days, the lowest price for a flight from Vail to Chicago was $221 for a one-way ticket and $340 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

  • Which airline alliances offer flights from Vail to Chicago?

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

  • On which days can I fly direct from Vail to Chicago?

    You can catch a nonstop flight from Vail to Chicago on on Saturday.

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

    The two airlines most popular with KAYAK users for flights from Vail to Chicago are United Airlines and American Airlines. With an average price for the route of $439 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 $388 and an overall rating of 7.2.

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

    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 Vail to Chicago.

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

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

    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 Chicago with an airline and back to Vail with another airline.

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

    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 Chicago from Vail 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 Vail to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $249 or less one-way and $308 or less round-trip.

Prefer to fly direct from Vail to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Vail Eagle County to Chicago.
Find which airlines fly direct from Vail Eagle County Airport to Chicago, which days they fly and book direct flights.

Direct departures

Vail Eagle County to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Vail Eagle County

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top airlines flying from Vail to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Vail to Chicago. 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 Vail to Chicago? 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 8999 reviews
7.7Boarding
8.1Crew
6.6Food
7.3Comfort
7.1Entertainment
Airline reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

10.0 ExcellentDr. Joseph, Oct 2025STL - ORD
Read more United Airlines reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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

Information on your arrival and departure airports

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