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$151+ Cheap flights from Vail (EGE) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Vail to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Vail (EGE) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$249
(American Airlines)

One-way from

$151
(American Airlines)

Popular in

May

Cheapest in

September

Average price

$213
From Vail Eagle County to Chicago (CHI)
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One-way flight from Vail Eagle County to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Vail to Chicago

Cheapest flights from Vail to Chicago
Explore the most affordable flight options available from Vail to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/110:27 amEGE - ORD
1 stop7h 08mAmerican Airlines
Fri 7/48:05 amORD - EGE
1 stop7h 11mAmerican Airlines
Deal found 6/10$249
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/238:50 amEGE - ORD
Nonstop2h 51mUnited Airlines
Wed 8/272:53 pmORD - EGE
1 stop6h 19mUnited Airlines
Deal found 6/12$319
This United deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:25 amEGE - ORD
2 stops8h 40mMultiple Airlines
Fri 8/1510:00 amORD - EGE
2 stops11h 40mMultiple Airlines
Deal found 6/12$1,048

Cheapflights Fare Finder

Customize your flight search to find flights from Vail to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Vail to Chicago that are best for you.

Fly from

Vail

Fly to

Chicago

Route

Depart

Return

Price

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 7/1

10:27 am-6:35 pm

1 stop7h 08m

Chicago O'Hare Intl

Fri 7/4

8:05 am-2:16 pm

1 stop7h 11m

$249

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 7/10

7:25 am-3:05 pm

1 stop6h 40m

Chicago O'Hare Intl

Sun 7/13

8:45 am-12:37 pm

1 stop4h 52m

$403

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 7/19

7:25 am-5:09 pm

2 stops8h 44m

Chicago O'Hare Intl

Mon 7/21

10:00 am-8:40 pm

2 stops11h 40m

$1,167

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 8/12

8:15 am-3:50 pm

1 stop6h 35m

$151

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 7/26

8:50 am-12:38 pm

Nonstop2h 48m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from Vail to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Vail with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Vail to Chicago?

Currently, August is the cheapest month in which you can book a flight from Vail to Chicago (average of $245). Flying from Vail to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EGE to CHI?

Find hourly flight availability from Vail to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Vail to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 4% on your trip compared to booking a flight at noon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines from Vail to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,790 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,790 reviews
United Airlines
7.4
Good
8,790 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,790 reviews

Food

6.6

Boarding

7.7

Comfort

7.3

Overall

7.4

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Vail to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Vail to Chicago?

    Most people fly from Vail Eagle County (EGE) if they book a flight from Vail to Chicago. On average, Eagle County has 0 outbound flights to Chicago per day from 2 airlines. Vail Eagle County is conveniently located just 28.9 mi from Vail’s city center.

  • What are the cheapest airlines flying from Vail to Chicago round-trip?

    Currently priced at $249, American Airlines will fly you from Vail to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $319.

  • What are the most reliable airlines from Vail to Chicago?

    Consider United Airlines (100%), American Airlines (0%) or Qatar Airways (0%) when booking your flight. These represent the most reliable airlines when flying from Vail to Chicago.

  • Can I find deals for flights from Vail to Chicago that include hotel bookings?

    Yes. In addition to deals on Vail to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vail to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vail to Chicago.

  • Can I find deals for business class flights from Vail to Chicago?

    Yes. Cheapflights offers flight deals from Vail to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Vail to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Vail to Chicago (average of $245). Flying from Vail to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Vail?

Book flights to Vail if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Top 2 airlines flying from Vail to Chicago

Discover the top 2 airlines that operate flights from Vail to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$348Average$555FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$484FlexibilityNo cancel feeOn-time71%

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