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$68+ Cheap flights from Vail (EGE) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$68
(Frontier)
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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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 January 21, 2025.

This Frontier deal was found by Cheapflights users on 1/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/172:58 pmEGE - ORD
1 stop8h 17mFrontier
Sun 4/206:45 amORD - EGE
1 stop8h 23mFrontier
Deal found 1/18$134
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/23:28 pmEGE - MDW
1 stop7h 49mFrontier
Thu 2/67:15 amMDW - EGE
1 stop8h 23mFrontier
Deal found 1/20$170
This American Airlines deal was found by Cheapflights users on 1/19. 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.
Thu 2/2012:35 pmEGE - ORD
Nonstop2h 38mAmerican Airlines
Mon 2/2410:15 amORD - EGE
Nonstop3h 02mAmerican Airlines
Deal found 1/19$329
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/192:56 pmEGE - ORD
1 stop7h 52mDelta
Mon 2/247:05 amORD - EGE
1 stop7h 46mDelta
Deal found 1/20$349
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 2/211:32 pmEGE - ORD
1 stop6h 55mUnited Airlines
Mon 2/247:00 amORD - EGE
1 stop4h 47mUnited Airlines
Deal found 1/20$359
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/192:56 pmEGE - MDW
1 stop6h 24mDelta
Mon 2/246:00 amMDW - EGE
1 stop8h 51mDelta
Deal found 1/20$454
This Travelocity deal was found by Cheapflights users on 1/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/56:48 pmEGE - ORD
2 stops17h 16mMultiple Airlines
Sun 3/96:45 amORD - EGE
1 stop8h 22mMultiple Airlines
Deal found 1/19$472
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/196:48 pmEGE - ORD
2 stops17h 16mAlaska Airlines
Mon 2/247:00 pmORD - EGE
2 stops41h 44mAlaska Airlines
Deal found 1/19$770

Find flights from Vail to Chicago within your budget

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 January 21, 2025.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 4/17

2:58 pm-12:15 am

1 stop8h 17m

Chicago O'Hare Intl

Sun 4/20

6:45 am-2:08 pm

1 stop8h 23m

$134

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 2/2

3:28 pm-12:17 am

1 stop7h 49m

Chicago Midway

Thu 2/6

7:15 am-2:38 pm

1 stop8h 23m

$170

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Thu 2/20

12:35 pm-4:13 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 2/24

10:15 am-12:17 pm

Nonstop3h 02m

$329

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 2/19

2:56 pm-11:48 pm

1 stop7h 52m

Chicago O'Hare Intl

Mon 2/24

7:05 am-1:51 pm

1 stop7h 46m

$349

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Fri 2/21

1:32 pm-9:27 pm

1 stop6h 55m

Chicago O'Hare Intl

Mon 2/24

7:00 am-10:47 am

1 stop4h 47m

$359

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Wed 2/19

2:56 pm-10:20 pm

1 stop6h 24m

Chicago Midway

Mon 2/24

6:00 am-1:51 pm

1 stop8h 51m

$454

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 3/5

6:48 pm-1:04 pm

2 stops17h 16m

Chicago O'Hare Intl

Sun 3/9

6:45 am-2:07 pm

1 stop8h 22m

$472

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Wed 2/19

6:48 pm-1:04 pm

2 stops17h 16m

Chicago O'Hare Intl

Mon 2/24

7:00 pm-11:44 am

2 stops41h 44m

$770

VailChicago

EGE - ORD

EGEORD

Vail Eagle County

Sun 2/2

3:28 pm-12:32 am

1 stop8h 04m

$91

VailChicago

EGE - MDW

EGEMDW

Vail Eagle County

Sun 2/2

3:28 pm-12:17 am

1 stop7h 49m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 15 results
1
2
  • Most accurate provider: When it comes to deals on Vail-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Vail-Chicago flight deals on Cheapflights vs. Expedia <90% 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.

Travel insights for flights from Vail to Chicago

Get recent, data-driven insights about flights from Vail to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 January 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Vail to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 28% on your trip compared to booking a flight in the morning.

Weekly flight availability from Vail to Chicago

Explore weekly flight availability from Vail to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 21, 2025.

The most flights from EGE to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 January 21, 2025.
Read reviews from past customers who have flown Frontier, American Airlines and Delta 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.
Alaska Airlines
8.0
Very good
9,696 reviews

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,696 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,521 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,982 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Frontier
6.1
Okay
3,440 reviews
Alaska Airlines
8.0
Very good
9,696 reviews

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 2 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 $68, Frontier will fly you from Vail to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Delta - these airlines can fly you to your destination from $329 and $349, respectively.

  • What are the cheapest airlines to fly from Vail to Chicago one-way?

    $91 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $273 and $285, respectively.

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

    Consider United Airlines (63%), American Airlines (41%) or Qatar Airways (30%) 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 $208. While the most popular route (Vail Eagle County - Chicago O'Hare Intl) can be booked for $334 on average our data indicates $438 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Vail to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$350Average$411FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$430Average$529FlexibilityNo cancel feeOn-time69%
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