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EGE - CHI

Find cheap flights from Vail to Chicago from $244

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 6/6. 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
0 bags
Fri 6/7
Fri 6/14

Search 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
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:17 pm - 6:55 pmEGE-ORD
4h 38m1 stop
5:04 am - 10:50 amORD-EGE
6h 46m1 stop
$380United Airlines
Find Deal
Wed, Jun 19 - Sun, Jun 23
1:17 pm - 9:04 pmEGE-ORD
6h 47m1 stop
3:50 pm - 5:54 pmORD-EGE
3h 04mnonstop
$390United Airlines
Find Deal
Wed, Jun 19 - Sat, Jun 22
12:43 pm - 8:45 pmEGE-ORD
7h 02m1 stop
6:25 am - 12:03 pmORD-EGE
6h 38m1 stop
$412American Airlines
Find Deal
Fri, May 24 - Mon, May 27
8:26 am - 3:40 pmEGE-ORD
6h 14m1 stop
3:15 pm - 8:05 pmORD-EGE
5h 50m1 stop
$420American Airlines
Find Deal
Sun, Jun 30 - Sat, Jul 6
2:39 pm - 9:25 pmEGE-ORD
5h 46m1 stop
7:00 am - 1:59 pmORD-EGE
7h 59m1 stop
$444American Airlines
Find Deal
Thu, Jun 20 - Sun, Jun 23
11:35 am - 6:55 pmEGE-ORD
6h 20m1 stop
3:50 pm - 5:54 pmORD-EGE
3h 04mnonstop
$470United Airlines
Find Deal
Wed, Jun 12 - Sat, Jun 15
9:00 am - 12:44 pmEGE-ORD
2h 44mnonstop
3:50 pm - 5:54 pmORD-EGE
3h 04mnonstop
$481United Airlines
Find Deal
Sun, Jun 30 - Sat, Jul 6
9:00 am - 12:44 pmEGE-ORD
2h 44mnonstop
7:10 am - 12:25 pmORD-EGE
6h 15m1 stop
$490United Airlines
Find Deal
Sun, Jun 30 - Sat, Jul 6
1:35 pm - 7:10 pmEGE-ORD
4h 35m1 stop
7:10 am - 10:36 amORD-EGE
4h 26m1 stop
$500United Airlines
Find Deal
Mon, May 20 - Wed, May 22
3:15 pm - 10:55 pmEGE-ORD
6h 40m1 stop
3:50 pm - 5:54 pmORD-EGE
3h 04mnonstop
$510United Airlines
Find Deal
Wed, Jul 10 - Sat, Jul 13

Flights from Vail to Chicago - Travel Insights & Trends

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 one-way flights from Vail to Chicago.
Our data shows that the cheapest route for a one-way flight from Vail to Chicago cost $161 and was between Vail and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $470.

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

The average price of all flights from Vail to Chicago clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Vail to Chicago, look for departures on Sundays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago, Sunday is the cheapest day to fly and Thursday is the most expensive.

Which airlines provide the cheapest flights from Vail to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on American Airlines ($244) and United Airlines ($370). The cheapest round-trip tickets were found on United Airlines ($380) and American Airlines ($412).

Which airlines fly non-stop between Vail and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Vail to Chicago.
There is just one airline that flies from Vail to Chicago direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $430.

How many flights are there between Vail and Chicago per day?

There is a maximum of 1 nonstop flight a day that takes off from Vail and lands in Chicago, with an average flight time of 2h 44m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 2 flights.

Which cabin class options are there for flights between Vail and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Vail to Chicago take?

The average nonstop flight takes 2h 44m, covering a distance of 1,018 miles.

What’s the earliest departure time from Vail to Chicago?

Early birds can take the earliest flight from Vail at 9:00 am and will be landing in Chicago at 12:44 pm.

What’s the latest departure time from Vail to Chicago?

If you prefer to fly at night, the latest flight from Vail to Chicago jets off at 9:00 am and lands at 12:44 pm.

Good to know

Low season

November

High season

August

Cheapest flight

$244
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 14% increase in price.
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 $380 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 $480 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 $622 and an overall rating of 7.3.

  • 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.

See more FAQs

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 $242 or less one-way and $484 or less round-trip.

Prefer to fly non-stop from Vail to Chicago?

Find which airlines fly direct from Eagle County to Chicago, which days they fly and book direct flights.

Nonstop departures

Vail Eagle County to Chicago

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Nonstop 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 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 11043 reviews
6.7Food
7.2Comfort
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

8.0 ExcellentMichelle, Apr 2024MBS - ORD
Read more about United Airlines reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Vail to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Vail to Chicago found on KAYAK in the last 72 hours.
6/6Thu
1 stopAmerican Airlines
5h 46mEGE-ORD
$244
8/3Sat
1 stopAmerican Airlines
5h 36mEGE-ORD
$264
5/15Wed
1 stopAmerican Airlines
7h 02mEGE-ORD
$346
6/7Fri
2 stopsUnited Airlines
19h 24mEGE-ORD
$370
5/13Mon
1 stopAmerican Airlines
5h 38mEGE-ORD
$393
8/3Sat
2 stopsUnited Airlines
17h 06mEGE-ORD
$425
6/6Thu
2 stopsUnited Airlines
17h 42mEGE-ORD
$440
5/15Wed
2 stopsAmerican Airlines
18h 32mEGE-ORD
$447
6/20Thu
2 stopsUnited Airlines
23h 08mEGE-ORD
$458
5/13Mon
2 stopsUnited Airlines
17h 45mEGE-ORD
$468

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Vail - Chicago Flights

Departure:

Vail (undefined)United States

Cabin classes:

$1,305
$470