ORD - EGE

$208 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 5/12. 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 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$389
Typical prices: $440-$381
American Airlines
Fri 5/15Tue 5/19
ORD - EGE • 1 stop
Cheapest non-stop
$554
United Airlines
Fri 7/31Sun 8/2
ORD - EGE • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Nonstop flights
Fri, Sat
You can fly direct with United Airlines. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $389 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 26% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Expert advice
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

Fri, May 15 - Tue, May 19
American Airlines Logo
12:30 pm - 7:09 pm
ORD
-
EGE
7h 39m
1 stop
American Airlines Logo
8:00 am - 3:18 pm
EGE
-
ORD
6h 18m
1 stop
$389American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
8:19 am - 1:31 pm
ORD
-
EGE
6h 12m
1 stop
American Airlines Logo
2:12 pm - 10:10 pm
EGE
-
ORD
6h 58m
1 stop
$404American Airlines
Thu, Jun 4 - Sun, Jun 7
American Airlines Logo
11:40 am - 7:04 pm
ORD
-
EGE
8h 24m
1 stop
American Airlines Logo
2:12 pm - 11:37 pm
EGE
-
ORD
8h 25m
1 stop
$424American Airlines
Fri, Jun 12 - Tue, Jun 16
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
United Airlines Logo
3:25 pm - 9:54 pm
EGE
-
ORD
5h 29m
1 stop
$442United Airlines
Tue, Jun 2 - Sun, Jun 7
American Airlines Logo
1:25 pm - 7:04 pm
ORD
-
EGE
6h 39m
1 stop
American Airlines Logo
7:50 am - 3:44 pm
EGE
-
ORD
6h 54m
1 stop
$462American Airlines
Sun, Jun 28 - Fri, Jul 3
American Airlines Logo
8:19 am - 1:31 pm
ORD
-
EGE
6h 12m
1 stop
American Airlines Logo
2:12 pm - 9:13 pm
EGE
-
ORD
6h 01m
1 stop
$465American Airlines
Fri, Jun 5 - Mon, Jun 8
United Airlines Logo
4:00 pm - 6:05 pm
ORD
-
EGE
3h 05mnonstop
United Airlines Logo
3:25 pm - 11:19 pm
EGE
-
ORD
6h 54m
1 stop
$469United Airlines
Thu, Jun 4 - Sun, Jun 7
American Airlines Logo
7:02 am - 1:31 pm
ORD
-
EGE
7h 29m
1 stop
American Airlines Logo
2:12 pm - 11:37 pm
EGE
-
ORD
8h 25m
1 stop
$489American Airlines
Tue, Apr 28 - Sat, May 2
American Airlines Logo
12:30 pm - 7:09 pm
ORD
-
EGE
7h 39m
1 stop
American Airlines Logo
8:00 am - 3:18 pm
EGE
-
ORD
6h 18m
1 stop
$499American Airlines
Fri, May 8 - Sun, May 17
American Airlines Logo
11:43 am - 7:09 pm
ORD
-
EGE
8h 26m
1 stop
American Airlines Logo
8:00 am - 3:18 pm
EGE
-
ORD
6h 18m
1 stop
$509American Airlines
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Vail?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Vail departing in May.

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 Sunday and more expensive on a Thursday. On your return trip to Chicago, you should consider flying back on a Sunday, and avoid Saturdays 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 September, where tickets cost $309 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $594 and $539 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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Vail

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Good to know

Low seasonOctober
Cheapest flight$208
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 11% 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 $208 for a one-way ticket and $389 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, 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 $469 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 $420 and an overall rating of 7.1.

  • 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 $284 or less one-way and $344 or less round-trip.

Prefer to fly direct from Chicago to Vail?

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

Direct departures

Chicago O'Hare Intl to Vail Eagle County

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

Vail Eagle County to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

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 9581 reviews
7.1Entertainment
7.7Boarding
6.6Food
7.3Comfort
8.1Crew
Airline reviews

Poor communication, flight was delayed for preventable reasons. I missed my connection.

2.0 MediocreAaron, Apr 2026
ORD - BNA
Read more United Airlines reviews

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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

Information on your arrival and departure airports