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$194 Cheap Flights from Vail (EGE) to Chicago (ORD)

View $194 flight on Tue, Aug 18, 2026Opens in a new window

Popular airlines from Vail/Eagle Airport (EGE) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Vail to Chicago (EGE-ORD)

Prices were available within the past 7 days and start at $194 for one-way flights and $354 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Sep 10 - Mon, Sep 14
EGE
Vail
ORD
Chicago
$354 Roundtrip, found 8 hours ago
$354
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Thu, Sep 10 from Vail to Chicago, returning Mon, Sep 14, priced at $354 found 8 hours ago
American Airlines
Fri, Sep 4 - Sat, Sep 5
EGE
Vail
ORD
Chicago
$357 Roundtrip, found 8 hours ago
$357
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Vail to Chicago, returning Sat, Sep 5, priced at $357 found 8 hours ago
American Airlines
Thu, Sep 3 - Sun, Sep 6
EGE
Vail
ORD
Chicago
$366 Roundtrip, found 3 days ago
$366
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Sep 3 from Vail to Chicago, returning Sun, Sep 6, priced at $366 found 3 days ago
American Airlines
Fri, Sep 4 - Sat, Sep 5
EGE
Vail
ORD
Chicago
$369 Roundtrip, found 8 hours ago
$369
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Vail to Chicago, returning Sat, Sep 5, priced at $369 found 8 hours ago
American Airlines
Thu, Sep 10 - Mon, Sep 14
EGE
Vail
ORD
Chicago
$374 Roundtrip, found 8 hours ago
$374
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Thu, Sep 10 from Vail to Chicago, returning Mon, Sep 14, priced at $374 found 8 hours ago
American Airlines
Fri, Sep 4 - Sat, Sep 5
EGE
Vail
ORD
Chicago
$377 Roundtrip, found 8 hours ago
$377
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Sep 4 from Vail to Chicago, returning Sat, Sep 5, priced at $377 found 8 hours ago
American Airlines
Thu, Sep 10 - Mon, Sep 14
EGE
Vail
ORD
Chicago
$381 Roundtrip, found 8 hours ago
$381
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Thu, Sep 10 from Vail to Chicago, returning Mon, Sep 14, priced at $381 found 8 hours ago
American Airlines
Thu, Sep 10 - Mon, Sep 14
EGE
Vail
ORD
Chicago
$386 Roundtrip, found 8 hours ago
$386
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Thu, Sep 10 from Vail to Chicago, returning Mon, Sep 14, priced at $386 found 8 hours ago
Delta
Thu, Jan 21 - Tue, Jan 26
EGE
Vail
ORD
Chicago
$425 Roundtrip, just found
$425
Roundtrip
just found
Select Delta flight, departing Thu, Jan 21 from Vail to Chicago, returning Tue, Jan 26, priced at $425 just found
United
Thu, Jan 21 - Tue, Jan 26
EGE
Vail
ORD
Chicago
$499 Roundtrip, just found
$499
Roundtrip
just found
Select United flight, departing Thu, Jan 21 from Vail to Chicago, returning Tue, Jan 26, priced at $499 just found

What you need to know for your flight from Eagle County Regional to O'Hare Intl.

Vail (EGE) to Chicago (ORD) at a glance

Travel from Vail (EGE) to Chicago (ORD) with a selection of airlines offering various options on this domestic short-haul route. Discover flights to Chicago that suit your budget and schedule as you delve into the city's renowned attractions and neighborhoods. Explore the details for flights from Eagle County Regional Airport to O'Hare International Airport, and consider your choices for affordable Vail to Chicago airfare that aligns with your travel plans.

  • Fastest flight duration: around 2h 45m non-stop
  • Route distance: roughly 1,000 miles (1,610 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $165–$545, depending on seasonality and how far ahead you book

Flights from Eagle County Regional Airport (EGE) to O'Hare International Airport (ORD)

According to recent traveler bookings, here are the top airlines favored for flights from Vail to Chicago, featuring both non-stop and one-stop options. Popular layover cities include Denver International Airport (DEN) with an average layover of about 1 hour and 15 minutes, and Dallas-Fort Worth International Airport (DFW) offering a layover of approximately 1 hour and 45 minutes. This gives you the flexibility to choose based on price, total travel time, and cabin class to find your ideal itinerary.

  • United: This full-service airline provides both non-stop and one-stop options, with one-way fares generally between $165 and $555. United accounts for around 53% of flights on this route, featuring a typical non-stop travel duration of 2 hours and 45 minutes.
  • American Airlines: As a full-service carrier, American Airlines offers non-stop and one-stop services, with one-way ticket prices usually ranging from $165 to $525. They represent about 47% of departures on this route, typically with a non-stop travel time of 2 hours and 45 minutes.

Alternative route from Vail (EGE) to Chicago (ORD)

  • Aspen to Chicago (ASE-ORD): Pitkin County Airport (ASE) is located roughly 29 miles from Eagle County Regional Airport (EGE). One-way economy ticket prices for this route generally fall between $135 and $775, influenced by the season and timing of the booking. Passengers can choose from both non-stop and one-stop flight options. Leading airlines operating on this route include United and American Airlines. Additionally, premium service is offered for first class travelers on this route.

How to find the best prices for flights from Vail (EGE) to Chicago (ORD)

Getting some of the best deals on flights from Vail to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking 2-8 weeks in advance, which is also when most travelers make their reservations. Afternoon departures, between 12 PM and 6 PM, tend to be less expensive and are the most popular flight times. Additionally, flying on Thursday often results in lower prices, while Friday remains the busiest travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Eagle County Regional Airport

Chicago welcomes travelers from Vail with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From O'Hare International Airport, O'Hare Station (a metro station) is just about 0.1 miles away on foot, while for those traveling by car, Rosemont Station (a train station) is located approximately 2.2 miles from the airport.

Frequently asked questions

How much does a flight from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $194 and cheap return flights from $354 Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $231 to $850, and return flights typically cost between $477 and $1298. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from EGE to ORD is September when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Choose from 2 airlines operating direct flights from EGE to ORD:

  • United operates around 19 direct flights from EGE to ORD every week
  • American Airlines operates around 13 direct flights from EGE to ORD every week

What is the cheapest airline that flies from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering nonstop flights from Vail, CO (EGE) to Chicago, IL (ORD), with round-trip tickets starting from around $340. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Vail, CO (EGE) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. United also offers the most daily flights from EGE to ORD, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 3 nonstop flights per day from Eagle County Regional (EGE) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Eagle County Regional Airport (EGE) to O'Hare International Airport (ORD) typically departs at 7:00 AM, operated by United Airlines. This early flight can help you maximize your time in Chicago. This service is seasonal and operates in January and February. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Vail, CO (EGE) to Chicago, IL (ORD) are in the early afternoon, from 12pm to 3pm. About 42% of passengers prefer this time window. Many major carriers, including United Airlines and American Airlines, offer flights during this window. This timing works well because it gives you the morning to enjoy the slopes before heading to the airport.
How long does it take to fly from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from EGE to ORD usually take about 3 hours, traveling roughly 1,005 miles. If you opt for a connecting flight, expect to add around 3 hours 50 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly first class between EGE and ORD. First class cabins are available on:

  • American Airlines
  • United Airlines
  • Delta Air Lines

How do I earn miles on a Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Eagle County Regional (EGE)?
If you're planning to travel to Chicago from Eagle County Regional (EGE), you can fly into O'Hare Intl. (ORD) Some flights may connect through major hubs like Denver Intl. (DEN), Dallas-Fort Worth Intl. (DFW), San Diego Intl. (SAN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Vail, CO (EGE-Eagle County Regional) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Eagle County Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$354
Distance
1004 mi
Average flight time
2 hours 52 mins

Book with confidence

Vail to Chicago Flights

The cheapest times to fly from Vail to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Vail to Chicago are during the month of September. You can find some of the cheapest flights from Vail to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Vail to Chicago

Sunday is one of the best days to book for cheap flights from Vail to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Vail to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Vail to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $194 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Vail to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Vail to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Vail to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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