New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

undefined Itinerary

Last updated: 2024 Jun 14

Morning
Start the day with a visit to Millennium Park, Chicago's iconic public park, and take a selfie in front of the famous Cloud Gate sculpture, also known as the Bean. Afterward, head to the Art Institute of Chicago to admire some of the world's finest art collections, including works by Picasso, Van Gogh, and Monet.
Afternoon
Refuel with a Chicago-style hot dog or deep-dish pizza from Portillo's or Lou Malnati's, respectively. Then, take a stroll down the Magnificent Mile, Chicago's upscale shopping district, and explore the various shops and boutiques.
Evening
End the day with a sunset cruise along the Chicago River, where you can enjoy breathtaking views of the city's skyline while sipping on cocktails and learning about the city's history.
Bedtime
Find amazing hotels in .

Morning
Visit the Willis Tower, formerly known as the Sears Tower, and take a ride up to the Skydeck on the 103rd floor, where you can step out onto the Ledge, a glass balcony that extends out four feet from the building, offering stunning views of the city below.
Afternoon
Grab a bite to eat at the famous Billy Goat Tavern, an iconic Chicago institution that has been around since 1934. Afterward, head to Navy Pier, a 3,300-foot long pier that stretches out into Lake Michigan and offers various attractions, including rides, restaurants, and a Ferris wheel.
Evening
Catch a show at the Chicago Theatre, a landmark venue that has hosted some of the biggest names in entertainment since 1921, or head to one of Chicago's many comedy clubs, such as Second City or Zanies, for some laughs.
Bedtime
Find amazing hotels in .

Morning
Explore the Museum Campus, a collection of three world-class museums located in Grant Park, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.
Afternoon
Grab lunch at the famous Portillo's, known for its Chicago-style hot dogs and Italian beef sandwiches. Afterward, head to Wrigley Field, home of the Chicago Cubs, to catch a baseball game and experience the excitement of one of America's favorite pastimes.
Evening
End the day with a night out in Wicker Park, a trendy neighborhood known for its eclectic mix of restaurants, bars, and music venues. Check out the live music scene at the Double Door or catch a DJ set at the Subterranean.
Bedtime
Find amazing hotels in .

Morning
Take a stroll through the Lincoln Park Zoo, a free zoo that is home to over 200 species of animals. Afterward, explore the nearby Lincoln Park Conservatory, a beautiful indoor botanical garden.
Afternoon
Grab lunch at one of Chicago's famous delis, such as Manny's or The Bagel, and indulge in a classic corned beef sandwich. Afterward, head to the Museum of Science and Industry, the largest science museum in the Western Hemisphere, and explore the various exhibits and interactive displays.
Evening
End the day with a visit to the Second City, a legendary comedy club that has launched the careers of many famous comedians, including Bill Murray, Tina Fey, and Stephen Colbert.
Bedtime
Find amazing hotels in .

Morning
Take a day trip to the charming town of Galena, located about three hours outside of Chicago. Explore the town's historic district, which features numerous 19th-century buildings and quaint shops and restaurants.
Afternoon
Grab lunch at Fried Green Tomatoes, a southern-style restaurant that serves up delicious comfort food. Afterward, take a scenic drive along the Great River Road, which offers stunning views of the Mississippi River and the surrounding countryside.
Evening
End the day with a visit to one of Galena's many wineries, such as Galena Cellars or Massbach Ridge Winery, and enjoy a tasting of some of Illinois's finest wines.
Bedtime
Find amazing hotels in .
kayakFind the right stay during your trip.
Got a question about your trip?