EGE - CHI

$117 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 3/14. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$241
Overall average: $461
American Airlines
Fri 3/20Sun 3/22
EGE - ORD • Non-stop
Cheapest one-way
$117
Typical prices: $185-$284
Alaska Airlines
Sat 3/14
EGE - ORD • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Main Cabin Extra includes early boarding.
United's Economy Plus offers extra legroom for comfort.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
American Airlines
Cheapest • from $241 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines and United Airlines. Average duration is 2h 52m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
EGE
-
ORD
Cheapest
EGE
-
ORD
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Dallas (DFW)
Cheapest • Avg $371 (round-trip)
Denver (DEN)
Shortest trip • 4h 20m (one-way)
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, Mar 20 - Sun, Mar 22
American Airlines Logo
12:05 pm - 3:53 pm
EGE
-
ORD
2h 48mnonstop
American Airlines Logo
10:34 am - 12:40 pm
ORD
-
EGE
3h 06mnonstop
$241American Airlines
Fri, Mar 20 - Sun, Mar 22
United Airlines Logo
3:25 pm - 11:52 pm
EGE
-
ORD
7h 27m
1 stop
United Airlines Logo
7:40 pm - 9:47 pm
ORD
-
EGE
3h 07mnonstop
$251United Airlines
Thu, Mar 19 - Thu, Mar 26
United Airlines Logo
12:27 pm - 4:20 pm
EGE
-
ORD
2h 53mnonstop
United Airlines Logo
9:10 am - 11:20 am
ORD
-
EGE
3h 10mnonstop
$265United Airlines
Thu, Mar 19 - Thu, Mar 26
United Airlines Logo
6:11 pm - 11:52 pm
EGE
-
ORD
4h 41m
1 stop
United Airlines Logo
7:40 pm - 9:47 pm
ORD
-
EGE
3h 07mnonstop
$275United Airlines
Tue, Mar 31 - Thu, Apr 2
American Airlines Logo
12:05 pm - 3:53 pm
EGE
-
ORD
2h 48mnonstop
American Airlines Logo
10:34 am - 12:40 pm
ORD
-
EGE
3h 06mnonstop
$279American Airlines
Tue, Mar 31 - Thu, Apr 2
American Airlines Logo
12:30 pm - 8:40 pm
EGE
-
ORD
7h 10m
1 stop
American Airlines Logo
10:34 am - 12:40 pm
ORD
-
EGE
3h 06mnonstop
$289American Airlines
Tue, Mar 31 - Thu, Apr 2
American Airlines Logo
2:37 pm - 10:24 pm
EGE
-
ORD
6h 47m
1 stop
American Airlines Logo
6:10 am - 1:56 pm
ORD
-
EGE
8h 46m
1 stop
$299American Airlines
Tue, Mar 17 - Wed, Mar 18
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$340Delta
Mon, Mar 16 - Tue, Mar 17
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$378Delta
Fri, Mar 13 - Mon, Mar 16
Delta Logo
3:31 pm - 10:31 pm
EGE
-
MDW
6h 00m
1 stop
Delta Logo
6:00 am - 2:11 pm
MDW
-
EGE
9h 11m
1 stop
$669Delta
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.

How much is a round-trip flight from Vail to Chicago?

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

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 $284 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 Wednesday. On your return trip to Vail, you should consider flying back on a Sunday, and avoid Thursdays for better deals.

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 $354, 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

Low seasonOctober
Cheapest flight$117
Best time to beat the crowds with an average 26% drop 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 $117 for a one-way ticket and $241 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?

    There are nonstop flights from Vail to Chicago on a daily basis.

  • 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 $388 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.

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 $279 or less one-way and $331 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

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Vail Eagle County

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American 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 9341 reviews
6.6Food
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

8.0 ExcellentDarly, Feb 2026
LAX - ORD
Read more United Airlines reviews

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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

Information on your arrival and departure airports