$248 Find Cheap Flights from Vail to Chicago - Compare and Save

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

• Earliest: departs at 7:45 am and lands at 10:44 am
• Latest: departs at 1:05 pm and lands at 4:04 pm.

The flight takes about 2h 59m.

Two cabin classes are available on flights from Vail to Chicago:

• Economy Class
• First Class

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

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.

Round-trip flights from Vail to Chicago range from $414 to $649, with an average of $486 over the past 12 months. Anything below $414 counts as a good deal.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $473 round-trip, compared to $562 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–$50 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Morning is the busiest departure period on Vail to Chicago flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $497 to $1,378. That means the highest observed fare was about 3x higher than the lowest one.

American Airlines is the only airline on the Vail to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

One-way fares from Vail to Chicago are currently lower than usual. Average one-way flight prices are about $292, which is 7% below the typical average for this route.

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 averaging $63:

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

Near Chicago Midway Airport (MDW) — daily rates averaging $86:

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

Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

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

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).

Connecting flights from Vail to Chicago most commonly pass through:

• Denver Intl (DEN) - 68% of one-stop connections
• Dallas/Fort Worth (DFW) - 32% of one-stop connections

Yes. Flexible dates can save you up to 37% on flights from Vail to Chicago. Wednesday is the cheapest departure day at $414 round-trip on average, while Monday is the most expensive at $655, a difference of $241.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

2 airlines operate flights between Vail and Chicago. The airlines offering nonstop flights on this route include:

• United Airlines
• American Airlines

Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 5h 23m, compared with 6h 41m 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.

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

Among airlines operating Vail to Chicago flights:

• United Airlines: offers free seat selection
• American Airlines: offers free seat selection

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

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

• United Airlines: a cabin bag in Economy Class class
• American Airlines: a cabin bag in Economy Class class

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