$236 Cheap Flights from Chicago (ORD) to Vail (EGE)

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

Travel effortlessly from Chicago O'Hare International Airport (ORD) to Vail's Eagle County Regional Airport (EGE) with a range of airlines offering convenient one-way flights. Whether you're looking for affordable options or prefer full-service carriers, you can compare Chicago to Vail airfare to discover the itinerary that aligns with your budget and schedule. Get ready to explore the breathtaking sights and vibrant neighborhoods of Vail as you make your travel plans.

• Fastest flight duration: around 3 hours non-stop
• Route distance: roughly 1,000 miles (1,610 km)
• Flights per week: around 10 departures on average
• Typical fares (one-way): economy tickets often range from $125–$480, depending on seasonality and how far ahead you book

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

Based on recent traveler bookings, here are the top airlines frequently chosen for flights from Chicago to Vail, emphasizing both non-stop and one-stop options. Common layovers include Denver International Airport (DEN) with an average layover of about 1 hour and 15 minutes, and Dallas-Fort Worth International Airport (DFW), typically featuring a layover of around 1 hour and 45 minutes. This allows you to compare prices, total travel times, and cabin classes to find the ideal itinerary for your trip.

• United: This comprehensive airline provides both non-stop and one-stop options, with one-way fares generally between $150 and $535. United represents roughly 58% of departures on this route, boasting an average non-stop flight duration of 3 hours.
• American Airlines: Another full-service option, American Airlines offers non-stop and one-stop flights, with one-way ticket prices usually ranging from $125 to $435. They account for about 39% of the departures, with typical non-stop travel taking approximately 3 hours.
• Frontier Airlines: A budget carrier, Frontier Airlines provides one-stop service at one-way fares typically between $125 and $155. They cover around 2% of the departures, with an in-flight duration of 3 hours 45 minutes and a total travel time of about 5 hours, including layovers.

Travelers flying from Chicago to Vail have the option to enhance their experience with an upgrade. United Airlines provides first-class service on this route.

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

• Chicago to Aspen (ORD-ASE): Pitkin County Airport (ASE) is located approximately 29 miles from Eagle County Regional Airport (EGE). One-way economy tickets for this route generally fall between $130 and $535, depending on the season and how far in advance you book. Travelers can choose between non-stop and one-stop flights. Major airlines operating this route include United and American Airlines, with first-class service also offered.

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

Getting some of the best deals on flights from Chicago to Vail 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 coincides with when most travelers make their reservations. Morning departures from 5 a.m. to 12 p.m. tend to offer lower prices and are also the most popular. Additionally, flying on Monday generally provides cheaper rates, while Thursday is the most favored 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.* Find Vail hotel and flight deals.
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 Eagle County Regional Airport from O'Hare International Airport

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

• Hotel transfer: Transfers offer a convenient way to reach your hotel in Vail, with options including free hotel shuttles and private rides, which can be arranged in advance with your hotel.
• Car rental: Renting a car from Eagle County Regional Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Eagle County Regional 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.

Chicago to Vail Flights

The cheapest times to fly from Chicago to Vail

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 Chicago to Vail are during the month of January. You can find some of the cheapest flights from Chicago to Vail with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Vail

Sunday is one of the best days to book for cheap flights from Chicago to Vail: 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 Chicago to Vail

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 Chicago to Vail in 2026. You can also book with separate airlines for your outbound and return journeys, from $236 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 Chicago to Vail 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 Chicago to Vail 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.