EGE - CHI

$208 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 9/2. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$410
American Airlines
Fri 10/2Mon 10/5
EGE - ORD • 1 stop
Cheapest non-stop
$569
United Airlines
Sat 8/1Fri 8/7
EGE - ORD • Non-stop
Nonstop flights
2 days a week
Sat, Sun
You can fly direct with United Airlines. Average duration is 2h 52m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $410 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
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!
Flight Deals
Booking Insights
Expert advice
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, Oct 2 - Mon, Oct 5
American Airlines Logo
12:58 pm - 8:30 pm
EGE
-
ORD
6h 32m
1 stop
American Airlines Logo
10:05 pm - 12:03 pm
ORD
-
EGE
14h 58m
2 stops
$410American Airlines
Wed, Jul 29 - Tue, Aug 4
American Airlines Logo
2:12 pm - 9:22 pm
EGE
-
ORD
6h 10m
1 stop
American Airlines Logo
1:25 pm - 6:50 pm
ORD
-
EGE
6h 25m
1 stop
$415American Airlines
Wed, Jul 29 - Tue, Aug 4
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
11:00 am - 6:50 pm
ORD
-
EGE
8h 50m
1 stop
$435American Airlines
Thu, Jul 9 - Mon, Jul 20
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$452American Airlines
Fri, Jul 17 - Mon, Jul 20
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$463American Airlines
Sat, Jul 4 - Wed, Jul 8
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
6:00 am - 12:03 pm
ORD
-
EGE
7h 03m
1 stop
$489United Airlines
Fri, Jul 24 - Sun, Jul 26
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$493American Airlines
Thu, Jul 2 - Thu, Jul 9
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$499American Airlines
Fri, Jul 17 - Thu, Jul 23
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$500American Airlines
Fri, Jul 3 - Sun, Jul 5
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
5:00 am - 9:53 am
ORD
-
EGE
5h 53m
1 stop
$510American Airlines
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 $376 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 Thursday and more expensive on a Saturday. On your return trip to Vail, you should consider flying back on a Sunday, and avoid Thursdays for better deals.

What is the cheapest month to fly from Vail to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Vail to Chicago, 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 Vail to Chicago is October, where tickets cost $0 (return) on average. On the other hand, the most expensive months are May and January, where the average cost of round-trip tickets is $682 and $536 respectively.

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 $650, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Vail to Chicago

 
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
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.

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.

Good to know

Cheapest flight$208
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 5 days, the lowest price for a flight from Vail to Chicago was $208 for a one-way ticket and $410 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?

    American Airlines, and JetBlue offer 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, 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 $456 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 7.1.

  • 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 $459 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

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 9860 reviews
7.3Comfort
7.7Boarding
6.7Food
7.1Entertainment
8.1Crew
Airline reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

10.0 ExcellentJoanne, Jun 2026
DEN - ORD
Read more United Airlines reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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

Information on your arrival and departure airports