Chicago Architecture Center River Cruise
See Chicago’s architecture from the river on a guided cruise aboard First Lady.
Explore Chicago Architecture Center River Cruise (opens the website in a new tab)
The destination · IL
Chicago
See Chicago’s architecture from the river and explore its art collections before settling into a downtown hotel.
Time well spent
Make time for Chicago.
Art Institute of Chicago
Explore the museum’s collection, with artworks from across the world.
Explore Art Institute of Chicago (opens the website in a new tab)Wrigley Field
Catch a Cubs game at the North Side ballpark that opened in 1914.
Explore Wrigley Field (opens the website in a new tab)Stay a little longer
Places to stay.
The Peninsula Chicago
A hotel on the Magnificent Mile, positioned for a stay centered on downtown Chicago.
Explore the hotel (opens the website in a new tab)The Langham, Chicago
A central Chicago hotel with a spa and indoor pool for time between city outings.
Explore the hotel (opens the website in a new tab)Find your airport
Where are you staying?
Pick a neighborhood to see the closest field and the drive.
Loading the map…
MDWClosest
Chicago Midway International
The close airport for the city, on the southwest side about 10 miles from the Loop. It wins for downtown, River North, the West Loop, the Gold Coast, Lincoln Park and the South Side.
- The Loop25 to 35 min
On the ground
The FBOs sit on their own side of the field, away from the airline terminal, so you never see it. The longest runway is about 6,500 feet, which handles light through heavy jets, though some heavy jets need a lighter load than they would at O'Hare.
PWKClosest
Chicago Executive
The north suburban field in Wheeling, with no airline traffic. It wins for the North Shore, Northbrook, Deerfield and Lake Forest, which are about 15 to 25 minutes away.
- The North Shore15 to 25 min
- Northbrook and Deerfield15 to 25 min
- The Loop40 to 50 min
On the ground
No airline traffic, so it stays calm when Midway is backed up by weather. The runway is about 5,000 feet, fine for light and midsize jets and for many super midsize jets on a dry day.
ORDClosest
Chicago O’Hare International
The big airport on the northwest side. It wins for an international connection, for the largest long range jets and for plans near the field.
- The Loop30 to 45 min
- Northbrook and Deerfield25 to 30 min
On the ground
One FBO, away from the airline terminals. Airline traffic means long taxi times and occasional holds, so allow extra time on both ends.
When to go
The season in Chicago.
- Chicago flies year round, and business travel sets the base.
- In winter the flow runs south to Florida and the desert, from Thanksgiving through Easter.
- The tightest weeks are Christmas through New Year, Presidents Day weekend and the March spring breaks.
- Summer flips the route, as winter residents of Florida head back north to the lake for July and August.
- Inbound, big conventions and game weekends fill the hotels and the ramps.
- In the peak weeks aircraft are spoken for early and prices sit in the upper half of the range.
Popular routes
Fly to Chicago.Fly from Chicago.
- 1 hr 5 min1 hr1 hr
- 1 hr 55 min1 hr 50 min1 hr 45 min
- 2 hr 35 min2 hr 30 min2 hr 25 min
Time in the air in calm conditions, rounded to five minutes. Your quote sets the schedule.
- 01
The Loop, the Gold Coast and Lincoln Park are a Midway trip. The North Shore and the northern suburbs are a Chicago Executive trip. The drive decides it.
- 02
From December to March expect deicing. It adds 20 to 40 minutes on the ground before departure and shows on the quote when it is needed.
- 03
Lake effect snow and low cloud can close a window at Chicago Executive while Midway stays open. On a marginal winter day we plan Midway.
- 04
Summer thunderstorms build across the Midwest in the afternoon. A morning arrival and an early evening departure are the calm ones.
- 05
O'Hare is possible but rarely the right choice for the city. It is farther from downtown and busier with airline traffic.
- 06
Chicago is on Central time, like Nashville and Dallas. Coming from Naples, which is on Eastern time, you gain an hour.
Plan your flight
Fly to Chicago.
Add where you are starting, a date and a headcount. Your starting prices arrive by email, and a pilot follows up as soon as the desk can review your request.
Fair questions
Chicago questions.
Midway or Chicago Executive?
Midway (MDW) for the Loop, River North, the West Loop and the South Side, about 25 to 35 minutes to downtown. Chicago Executive (PWK) for the North Shore and the northern suburbs, with no airline traffic. Tell us the address and we choose.
How much does a private jet to Chicago cost?
Your emailed planning estimate shows the current range by aircraft category once you enter where you are starting and your dates. A longer leg or a larger cabin sits higher in the range, and peak weeks sit in the upper half. Your quote will be exact.
How far ahead should I book for Chicago?
Two to four days is usually enough. For Thanksgiving, the weeks around Christmas and New Year, and a big game weekend, give us one to two weeks.
What happens if winter weather affects the trip?
We watch the forecast the day before and talk through timing with you. Deicing is routine and adds time on the ground, not risk. If snow or low cloud closes Chicago Executive, we plan Midway. The operator's crew makes the final call on the day, and we keep you posted.