EGE - CHI

$244 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 7/26. 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 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 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

Tue, Jul 1 - Sat, Jul 5
American Airlines Logo
8:15 am - 3:01 pmEGE-ORD
5h 46m1 stop
American Airlines Logo
5:00 am - 9:42 amORD-EGE
5h 42m1 stop
$265American Airlines
Find Deal
Tue, Jul 1 - Sat, Jul 5
United Airlines Logo
7:25 am - 3:05 pmEGE-ORD
6h 40m1 stop
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
$294United Airlines
Find Deal
Wed, Jul 23 - Tue, Jul 29
American Airlines Logo
8:15 am - 5:20 pmEGE-ORD
8h 05m1 stop
American Airlines Logo
5:00 am - 9:42 amORD-EGE
5h 42m1 stop
$335American Airlines
Find Deal
Fri, Sep 19 - Tue, Sep 23
American Airlines Logo
12:28 pm - 8:01 pmEGE-ORD
6h 33m1 stop
American Airlines Logo
11:54 am - 6:37 pmORD-EGE
7h 43m1 stop
$355American Airlines
Find Deal
Thu, Aug 28 - Sun, Aug 31
American Airlines Logo
10:30 am - 7:17 pmEGE-ORD
7h 47m1 stop
American Airlines Logo
8:20 am - 1:58 pmORD-EGE
6h 38m1 stop
$364American Airlines
Find Deal
Tue, Jul 1 - Mon, Jul 7
American Airlines Logo
8:15 am - 5:11 pmEGE-ORD
7h 56m1 stop
American Airlines Logo
5:00 am - 9:42 amORD-EGE
5h 42m1 stop
$365American Airlines
Find Deal
Mon, Jun 30 - Fri, Jul 4
United Airlines Logo
7:25 am - 9:10 pmEGE-ORD
12h 45m1 stop
United Airlines Logo
4:00 pm - 6:03 pmORD-EGE
3h 03mnonstop
$413United Airlines
Find Deal
Mon, Jun 30 - Fri, Jul 4
United Airlines Logo
7:25 am - 9:10 pmEGE-ORD
12h 45m1 stop
United Airlines Logo
10:56 am - 2:24 pmORD-EGE
4h 28m1 stop
$423United Airlines
Find Deal
Tue, Jul 1 - Sat, Jul 5
American Airlines Logo
8:15 am - 3:01 pmEGE-ORD
5h 46m1 stop
American Airlines Logo
9:55 am - 8:00 pmORD-EGE
11h 05m2 stops
$426American Airlines
Find Deal
Wed, Jul 23 - Tue, Jul 29
 Logo
7:25 am - 5:05 pmEGE-ORD
8h 40m2 stops
 Logo
8:42 pm - 8:40 pmORD-EGE
24h 58m2 stops
$1,027
Find Deal
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
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 $478 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 $478.

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$244
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 $244 for a one-way ticket and $265 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?

    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.

  • 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 $468 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.

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

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

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 8809 reviews
7.0Entertainment
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
Airline reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

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

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