$223 Find Cheap Flights from Vail to Chicago - Compare and Save

Among airlines operating Vail to Chicago flights:

• United Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only United Airlines operates flights between Vail and Chicago.

Flights from Vail to Chicago usually depart from Vail Eagle County (EGE) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Vail to Chicago.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $450 round-trip, compared to $561 via a layover through Dallas/Fort Worth (DFW).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$80 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Connecting flights from Vail to Chicago most commonly pass through:

• Denver Intl (DEN) - 74% of one-stop connections
• Dallas/Fort Worth (DFW) - 26% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

Yes. Being flexible with your travel dates can save you up to 43% on the Vail to Chicago route. Wednesday is the cheapest departure day at $374 round-trip on average, while Sunday is the most expensive at $650, a difference of $276. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

A nonstop flight from Vail to Chicago takes 2h 59m, covering 1,018 miles.

These are the earliest and latest flight times available from Vail to Chicago:

• Earliest: departs at 7:50 am and lands at 10:49 am
• Latest: departs at 8:00 am and lands at 10:59 am.

The flight takes about 2h 59m.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route varied from about $482 to $872. That means the highest observed fare was about 80% higher than the lowest one.

One-way fares from Vail to Chicago are currently lower than usual. Average one-way flight prices are about $234, which is 25% below the typical average for this route.

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 5h 20m, compared with 6h 43m via Dallas/Fort Worth (DFW).

Chicago is 1 hour ahead of Vail (Central Time vs Mountain Time). Plan for the time shift when scheduling connections or first-day activities.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

· Routes Car & Truck Rentals
· Europcar
· Hertz
· Dollar
· Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

· Alamo
· Enterprise Rent-A-Car
· Budget
· Avis
· National

Round-trip flights from Vail to Chicago range from $359 to $540, with an average of $476 over the past 12 months. Anything below $359 counts as a good deal.