EGE - CHI

$198 Find Cheap Flights from Vail to Chicago - Compare and Save

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 12/29. 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

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Everything you should know

Cheapest round-trip
$415
Typical prices: $604-$611
American Airlines
Thu 8/13Sun 8/16
EGE - ORD • 1 stop
Cheapest non-stop
$515
United Airlines
Sat 7/18Sat 7/25
EGE - ORD • Non-stop
Nonstop flights
3 days a week
Mon, 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 $415 (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
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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

Thu, Aug 13 - Sun, Aug 16
American Airlines Logo
7:50 am - 3:55 pm
EGE
-
ORD
7h 05m
1 stop
American Airlines Logo
8:20 am - 1:28 pm
ORD
-
EGE
6h 08m
1 stop
$415American Airlines
Thu, Jul 30 - Mon, Aug 3
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
Thu, Jul 30 - Mon, Aug 3
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
Tue, Jul 21 - Mon, Jul 27
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
$489American Airlines
Sat, Jul 18 - Sat, Jul 25
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 - Tue, Jul 21
American Airlines Logo
2:12 pm - 10:15 pm
EGE
-
ORD
7h 03m
1 stop
American Airlines Logo
12:05 pm - 6:50 pm
ORD
-
EGE
7h 45m
1 stop
$500American Airlines
Sat, Jul 18 - Sat, Jul 25
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
4:00 pm - 6:04 pm
ORD
-
EGE
3h 04mnonstop
$515United Airlines
Tue, Jul 28 - Sat, Aug 1
American Airlines Logo
2:12 pm - 11:39 pm
EGE
-
ORD
8h 27m
1 stop
American Airlines Logo
10:59 pm - 9:53 am
ORD
-
EGE
11h 54m
2 stops
$528American Airlines
Sat, Jul 18 - Sat, Jul 25
United Airlines Logo
8:00 am - 11:52 am
EGE
-
ORD
2h 52mnonstop
United Airlines Logo
6:59 am - 12:03 pm
ORD
-
EGE
6h 04m
1 stop
$531United Airlines
Thu, Jul 23 - 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
$534American 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 $416 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $650 on average.

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$198
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

  • 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 52m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 2 flights.

  • 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 $198 for a one-way ticket and $415 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 $359 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 $278 or less one-way and $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

Monday

United Airlines

United Airlines

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

Sunday

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 9927 reviews
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
6.7Food
Airline reviews

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

2.0 MediocreRuss, Jun 2026
FOD - ORD
Read more United Airlines reviews

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

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

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

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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.

We have taken this flight before and it is a tight connection and they were late out of denver and did not wait for us. The plane was there and the departure time had not passed but would not let us on. Next flight is very late and a connection through Newark - a big mess. Sooooo appreciate them holding the plane so we could catch the connection.

Upgrade planes to have larger overhead bins, especially on this popular route and first class. Easy flight to Chicago, good service in first class. Can't wait for seatback entertainment to be brought back. I like the free wifi and messaging with T-Mobile. Although, the tray tables are not big enough to work even on a small laptop - so why is it called "business" class?

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

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

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

Our flight from Eagle to Vail was delayed to the point we missed our connection to Savannah. Now we’re a family of 4 in a hotel room with luggage, no toiletries, no clean clothes. Gate attendant said the delay was mechanical but it was put in the system as something else so no compensation. That’s just wrong.

It was great. It was just a commuter so I splurged on first class and it was wonderful. Wish all seats were this spacious. Enjoyed it and will do it again.

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

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

Information on your arrival and departure airports