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

Currently priced at $389, United Airlines will fly you from Vail to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $437.

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

Travelers seeking maximum savings on their Vail to Chicago flight should consider departing on Wednesday mornings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Vail to Chicago?

Looking at all options, your cheapest flight can be booked for $155. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $289 on average our data indicates $596 when flying from Vail to Chicago.

What are the most reliable airlines from Vail to Chicago?

Consider United Airlines (72%), American Airlines (58%) or Qatar Airways (54%) when booking your flight. These represent the most reliable airlines when flying from Vail to Chicago.

What is the cheapest day to fly round-trip from Vail to Chicago?

It’s generally more expensive to depart on a Tuesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

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 1% on your trip compared to booking a flight at noon.

Most accurate provider : When it comes to deals on Vail-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Vail-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Vail-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Vail-Chicago flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Vail-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

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.

$208+ Flights from Vail to Chicago

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Cheap flight deals from Vail to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	Expedia 3 stars
Round-trip from	$389 (United Airlines)
One-way from	$266 (United Airlines)
Good round-trip deal	$568 or less
Good one-way deal	$480 or less

Provider with most accurate pricing for Vail Eagle County-Chicago (CHI) flight deals.

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Provider most trusted by Cheapflights users for Vail Eagle County-Chicago (CHI) flights.

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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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Price to beat on a round-trip flight from Vail Eagle County to Chicago (CHI).

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Price to beat on a one-way flight from Vail Eagle County to Chicago (CHI).

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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 April 24, 2025.

Sat 6/78:50 amEGE - ORD

Nonstop2h 48mUnited Airlines

Sat 6/144:00 pmORD - EGE

Nonstop3h 03mUnited Airlines

Deal found 4/22

$289

Wed 6/48:00 amEGE - ORD

2 stops11h 50mAmerican Airlines

Sat 6/71:28 pmORD - EGE

1 stop7h 29mAmerican Airlines

Deal found 4/23

$437

Best flights from Vail to Chicago
Discover carefully curated flight deals from Vail to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 24, 2025.

Fri 6/131:40 pmEGE - ORD

1 stop6h 40mUnited Airlines

Mon 6/162:33 pmORD - EGE

1 stop6h 28mUnited Airlines

Deal found 4/23

$389

Wed 6/48:00 amEGE - ORD

2 stops11h 50mAmerican Airlines

Sat 6/71:28 pmORD - EGE

1 stop7h 29mAmerican Airlines

Deal found 4/23

$437

Last-minute flights from Vail to Chicago
Discover last-minute flight deals from Vail to Chicago. Data last updated April 24, 2025 and is based on user searches.

Mon 4/281:45 pmEGE - ORD

2 stops24h 10mUnited Airlines

Fri 5/27:45 pmORD - EGE

1 stop17h 42mUnited Airlines

Deal found 4/22

$715

Tue 5/208:00 amEGE - ORD

1 stop8h 12mAmerican Airlines

Wed 5/211:58 pmORD - EGE

1 stop5h 54mAmerican Airlines

Deal found 4/22

$740

Sat 5/313:17 pmEGE - ORD

1 stop6h 24mUnited Airlines

Sun 6/17:10 amORD - EGE

1 stop6h 28mUnited Airlines

Deal found 4/22

$399

One-way flights from Vail to Chicago
Search for one-way flight options from Vail to Chicago. Find affordable one-way fares based on user searches. Data last updated April 24, 2025.

Sun 5/251:45 pmEGE - ORD

2 stops15h 45mUnited Airlines

Deal found 4/23

$266

Tue 5/208:00 amEGE - ORD

2 stops21h 19mAmerican Airlines

Deal found 4/22

$273

Cheapflights Fare Finder

Use the filters below to find and compare flights from Vail to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sat 6/7

8:50 am-12:38 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sat 6/14

4:00 pm-6:03 pm

Nonstop3h 03m

$289

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 6/4

8:00 am-8:50 pm

2 stops11h 50m

Chicago O'Hare Intl

Sat 6/7

1:28 pm-7:57 pm

1 stop7h 29m

$437

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Tue 5/20

8:00 am-8:50 pm

2 stops11h 50m

$208

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sun 5/25

1:45 pm-9:35 am

2 stops18h 50m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Compare providers for flights from Vail to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Vail to Chicago in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Vail-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Vail-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Vail-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Vail-Chicago flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Vail-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Rainfall in Chicago 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

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

United Airlines

7.4

Good

8,685 reviews

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

8,685 reviews

United Airlines

7.4

Good

8,685 reviews

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

8,685 reviews

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

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 $389, United Airlines will fly you from Vail to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $437.
What are the most reliable airlines from Vail to Chicago?
Consider United Airlines (72%), American Airlines (58%) or Qatar Airways (54%) when booking your flight. These represent the most reliable airlines when flying from Vail to Chicago.
What are the cheapest flights from Vail to Chicago?
Looking at all options, your cheapest flight can be booked for $155. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $289 on average our data indicates $596 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

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Porter

Lansing

Valparaiso

Chesterton

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Top 2 airlines flying from Vail to Chicago

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$348	Average$549	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$359	Average$501	FlexibilityNo cancel fee	On-time71%

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$208+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Vail to Chicago with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Vail to Chicago

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Good round-trip deal

Good one-way deal

Find flight deals from Vail to Chicago

Cheapest flights from Vail to ChicagoExplore 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 April 24, 2025.

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 April 24, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Vail to Chicago that are best for you.

Compare providers for flights from Vail to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Vail to Chicago in April.

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.

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?

Rainfall in Chicago by month

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

Temperature in Chicago by month

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

Reviews of airlines servicing Chicago

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?

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

What are the most reliable airlines from Vail to Chicago?

What are the cheapest flights from Vail to Chicago?

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

How can I find direct flights from Vail to Chicago?

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

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

Traveling to a place near Vail?

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Alternative routes for Vail to Chicago

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Top 2 airlines flying from Vail to Chicago

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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 April 24, 2025.