EGE - CHI

$275 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 7/18. 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

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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Vail to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Vail to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
10:25 am - 7:45 pmEGE-ORD
8h 20m1 stop
American Airlines Logo
5:00 am - 9:42 amORD-EGE
5h 42m1 stop
$309American Airlines
Find Deal
Thu, Jul 10 - Sun, Jul 13
United Airlines Logo
3:21 pm - 9:17 pmEGE-ORD
4h 56m1 stop
United Airlines Logo
8:45 am - 2:38 pmORD-EGE
6h 53m1 stop
$379United Airlines
Find Deal
Sat, May 10 - Tue, May 13
United Airlines Logo
8:50 am - 12:38 pmEGE-ORD
2h 48mnonstop
United Airlines Logo
8:45 am - 12:38 pmORD-EGE
4h 53m1 stop
$389United Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
7:25 am - 12:25 amEGE-ORD
16h 00m1 stop
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
$507United Airlines
Find Deal
Mon, May 26 - Sat, Aug 16
United Airlines Logo
7:25 am - 12:25 amEGE-ORD
16h 00m1 stop
United Airlines Logo
10:44 am - 2:24 pmORD-EGE
4h 40m1 stop
$517United Airlines
Find Deal
Mon, May 26 - Sat, Aug 16
United Airlines Logo
3:21 pm - 8:00 amEGE-ORD
15h 39m2 stops
United Airlines Logo
8:45 am - 12:27 pmORD-EGE
4h 42m1 stop
$520United Airlines
Find Deal
Sat, May 10 - Tue, May 13
United Airlines Logo
1:40 pm - 2:11 pmEGE-ORD
23h 31m2 stops
United Airlines Logo
8:45 am - 12:38 pmORD-EGE
4h 53m1 stop
$531United Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
United Airlines Logo
7:25 am - 12:25 amEGE-ORD
16h 00m1 stop
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
$552United Airlines
Find Deal
Mon, May 26 - Fri, Aug 15
United Airlines Logo
7:25 am - 12:25 amEGE-ORD
16h 00m1 stop
United Airlines Logo
8:45 am - 12:32 pmORD-EGE
4h 47m1 stop
$562United Airlines
Find Deal
Mon, May 26 - Fri, Aug 15
American Airlines Logo
10:25 am - 7:45 pmEGE-ORD
8h 20m2 stops
American Airlines Logo
5:00 am - 9:42 amORD-EGE
5h 42m1 stop
$633American Airlines
Find Deal
Thu, Jul 10 - Sun, Jul 13
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
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.

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.

Our travel experts
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
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
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Vail to Chicago.

Our data shows that the cheapest route for a return flight from Vail to Chicago cost $299 and was between Vail (EGE) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $299.

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 Wednesday 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.

Good to know

Cheapest flight$275
Flight from Vail to Chicago O'Hare Airport

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 $275 for a one-way ticket and $309 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 Airbus A319 is the aircraft model that flies most regularly on the Vail to Chicago flight route.

  • Which airline alliances offer flights from Vail to Chicago?

    Star Alliance is the only airline alliance operating flights between Vail and Chicago.

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

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

  • 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 $218 or less one-way and $568 or less round-trip.

Prefer to fly direct from Vail 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

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Vail Eagle County

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top airline 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 8696 reviews
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
Airline reviews

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

10.0 ExcellentDr. Joseph, Apr 2025IAH - ORD
Read more United Airlines reviews

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

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

Information on your arrival and departure airports

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