Chicago City Guide

Known for a rich culture that birthed performing arts scenes and world class cuisine, Chicago is a unique destination for teams to discover together.

Explore Chicago

One of the most iconic destinations in the United States, Chicago is a city of traditions. Your first visit there will be filled with classic sights and flavors that make this city what it is.

Indulging in the ooey-gooey goodness of a cheesy deep-dish pizza or a true Chicago-style hot dog, cruising the Chicago River aboard Chicago’s First Lady to admire the mesmerizing architecture—old and new, and wandering down The Magnificent Mile to find The Bean are just a few of the must-do activities.

The chill of The Windy City is real in the colder months, so pencil in your visit for warmer spring and summer days.

Spring: 45–55°F
Summer: 70–80°F
Autumn: 50–60°F
Winter: 25-35°F

Avg hotel cost

$$
Walk score

77
Transit score

65

Our favorite picks

Hotels

The Wit Hotel

Within blocks of Chicago staples like the John Daley Center, the Chicago Theatre, and the Willis Tower. Spectacular onsite features include the spa and salon, an in-house library, and an award-winning rooftop.

The Emily Hotel

A swanky and serene hotel that set down its roots in Chicago’s Fulton Market District of the West Loop, bringing uniquely-fresh hospitality experiences to a bustling area with locals and visitors alike.

The Robey

Possibly the most prime real estate in Wicker Park, the Robey Hotel is an Art Deco masterpiece yet brings a fresh, vibrant, new feel to the ever-bustling neighborhood.

Restaurants

River Roast

Situated on the iconic Chicago River with stunning views of downtown, River Roast is a lively social house and gathering place featuring contemporary American fare.

Blue Door Kitchen and Garden

A farm-to-table oasis where the seasons dictate the menu. Since its inception, the brand has become synonymous with sustainability and responsible sourcing.

Terzo Piano

Located on the rooftop of the Art Institute, this upscale spot boasts a modern, fresh design. Its spectacular location offers panoramic views of Lake Michigan.

Experiences

Art Institute of Chicago

The Art Institute of Chicago was founded in 1879 and is one of the oldest and largest art museums in the world. Recognized for its curatorial efforts and popularity among visitors, the museum hosts approximately 1.5 million people annually.

Chicago Theatre

This beautiful, historic movie palace hosts live performances and famous Broadway musicals such as Les Misérables, Aladdin, Chicago, and more.

Urban kayaking and boat tours

Explore the city from a unique point of view. Kayaks and private boat tours can take you for a scenic journey along the famous Chicago River to experience the views like never before.