< Back to Vacations

Chicago, the Windy City

Chicago is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers and all the offers of a word-class city. Its culture is unique, whether its deep dish pizza's or attempting to pile seven toppings on a hot dog. This city allows you to hang out with music fans at Lollapalooza, and in the next heartbeat relieve the Al Capone Era at the Green Mill Jazz Club in Uptown. Or watch a game and then work up a sweat along the waterfront trail. Chicago is a city to be experienced.

Trip Concierge Location Marker

Destination

Chicago, IL

Trip Concierge On/Off Button

Best Duration

2 Nights / 3 Days

Trip Concierge Blue Airplane

Departure Airports

All Major U.S. & Canadian Airports

Speak to a Travel Expert
3-Star Vacation Ideas
4-Star Vacation Ideas
5-Star Vacation Ideas

Smart Vacation

starting from

$900

Premium Vacation

starting from

$1215

Posh Vacation

starting from

$1550

Flights

Economy

Economy

Premium Economy

Featured Hotels

Fun Activities

Available Extras

Personal Shopping Experiences
Family Friendly Outings

Foodie Tours
Private Guided Tours

Sports & Adventure Activities
and so much more.

Speak with our Travel Experts

We'll do the pricing, planning and research for you.
Make an Appointment

or call 1-800-503-8173

Prices above are guidelines and subject to change until booked. Certain departure dates may increase the cost of the vacation, including choice of airline, routing, departure times and hotel room category. Smart and Premium Vacations were budgeted to include non-refundable return economy flights and one activity. Posh Vacations were budgeted to include non-refundable premium economy (extra legroom) flights, where available and one activity. Vacations are either for one (1) adult, two (2) adults or families with two (2) adults and up to two (2) children staying in the same room single, double or quadruple occupancy, respectively.