Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

7-Day High Budget Itinerary for Two in Chicago

Viewed by 108 travelers

Day 1: Sunday, November 5, 2023

Morning: Explore Millennium Park

Start your Chicago adventure by visiting Millennium Park in the morning. Admire the famous Cloud Gate sculpture, also known as "The Bean," and take some memorable photos. Enjoy a leisurely walk through the park's beautiful gardens and sculptures.

  • Millennium Park: $0, 2 hours
Afternoon: Art Institute of Chicago

Spend the afternoon exploring the world-renowned Art Institute of Chicago. Marvel at the vast collection of artworks, including famous masterpieces like Grant Wood's "American Gothic" and Vincent van Gogh's "The Bedroom."

  • Art Institute of Chicago: $25 per person, 3 hours
Evening: Navy Pier

As the evening sets in, head to Navy Pier for a fun-filled experience. Enjoy panoramic views of Lake Michigan, ride the Ferris wheel, and explore the various attractions, shops, and restaurants along the pier.

  • Navy Pier: Free admission, individual attraction costs and dining expenses may vary, 3 hours

Day 2: Monday, November 6, 2023

Morning: Magnificent Mile Shopping

Start your day with a shopping spree on the Magnificent Mile. Explore high-end fashion boutiques, luxury department stores, and local shops while enjoying the vibrant atmosphere of this iconic Chicago street.

  • Magnificent Mile: Cost varies depending on purchases, 2 hours
Afternoon: Chicago River Architecture Boat Tour

Immerse yourself in the architectural beauty of Chicago with a boat tour on the Chicago River. Cruise past stunning skyscrapers while learning about the city's rich architectural history from knowledgeable guides.

  • Chicago River Architecture Boat Tour: $50 per person, 1.5 hours
Evening: Chicago Symphony Orchestra

End your day with a memorable evening at the Chicago Symphony Orchestra. Enjoy a world-class performance in one of America's most esteemed concert venues.

  • Chicago Symphony Orchestra: Ticket prices vary, 2 hours

Day 3: Tuesday, November 7, 2023

Morning: Museum of Science and Industry

Spend the morning exploring the fascinating Museum of Science and Industry, known for its interactive exhibits and immersive experiences. Discover the wonders of science, technology, and innovation.

  • Museum of Science and Industry: $30 per person, 3 hours
Afternoon: Chicago Cultural Center

Visit the Chicago Cultural Center, a historic landmark filled with stunning architecture and artistic exhibitions. Admire the breathtaking Tiffany stained glass dome and explore the center's rotating art displays.

  • Chicago Cultural Center: Free admission, 2 hours
Evening: Chicago-style Deep Dish Pizza

Treat yourself to an authentic Chicago-style deep dish pizza for dinner. Indulge in this iconic local favorite, known for its thick crust, chunky tomato sauce, and generous cheese toppings.

  • Various pizza places: Cost varies depending on restaurant, 1.5 hours

Day 4: Wednesday, November 8, 2023

Morning: Adler Planetarium

Begin your day with a trip to the Adler Planetarium, where you can explore the wonders of the universe through interactive exhibits, immersive shows, and breathtaking space views.

  • Adler Planetarium: $35 per person, 3 hours
Afternoon: Field Museum of Natural History

Delve into natural history at the Field Museum, home to extensive collections and exhibitions showcasing everything from dinosaurs to ancient civilizations. Don't miss Sue, the largest T. rex skeleton ever discovered.

  • Field Museum of Natural History: $40 per person, 3 hours
Evening: Second City Comedy Club

End your day with laughter at the famous Second City Comedy Club, known for launching the careers of many comedy legends. Enjoy hilarious improv shows and stand-up performances.

  • Second City Comedy Club: Ticket prices vary, 2 hours

Day 5: Thursday, November 9, 2023

Morning: Wrigley Field Tour

Take a guided tour of Wrigley Field, the iconic home of the Chicago Cubs. Explore the stadium's historic features and learn about the team's rich baseball history.

  • Wrigley Field Tour: $35 per person, 1.5 hours
Afternoon: Lincoln Park Zoo

Visit the Lincoln Park Zoo, one of the oldest zoos in the United States. Enjoy a leisurely stroll through beautifully landscaped grounds while observing a wide range of animal species.

  • Lincoln Park Zoo: Free admission, 2 hours
Evening: Dinner at Alinea

Indulge in an unforgettable dining experience at Alinea, a three-Michelin-starred restaurant known for its innovative and artistic approach to cuisine. Treat your taste buds to a multi-course tasting menu.

  • Alinea: Expensive fine dining experience, reservation required, 3 hours

Day 6: Friday, November 10, 2023

Morning: Shedd Aquarium

Explore the Shedd Aquarium, home to a diverse array of marine life from around the world. Marvel at stunning exhibits featuring sharks, dolphins, penguins, and more.

  • Shedd Aquarium: $40 per person, 3 hours
Afternoon: Chicago Riverwalk

Take a leisurely stroll along the Chicago Riverwalk, a scenic promenade lined with cafes, bars, and artistic installations. Enjoy the waterfront views and grab a bite to eat at one of the many dining options.

  • Chicago Riverwalk: Cost varies depending on purchases, 2 hours
Evening: Skydeck Chicago

End your day with a breathtaking view of Chicago from the Skydeck on the 103rd floor of the Willis Tower. Step out onto the glass ledge for a thrilling experience.

  • Skydeck Chicago: $25 per person, 2 hours

Day 7: Saturday, November 11, 2023

Morning: Garfield Park Conservatory

Discover the lush tropical landscapes of the Garfield Park Conservatory. Explore the various themed gardens and admire an impressive collection of exotic plants and flowers.

  • Garfield Park Conservatory: Free admission, 2 hours
Afternoon: Chicago Breweries Tour

Embark on a tour of Chicago's thriving craft beer scene. Visit breweries such as Revolution Brewing, Goose Island Brewery, and Half Acre Beer Company, sampling a wide variety of locally brewed beers.

  • Chicago Breweries Tour: Cost varies depending on purchases, 3 hours
Evening: Chicago River Night Cruise

End your trip with a memorable night cruise along the Chicago River, admiring the city's beautifully illuminated skyline. Relax and enjoy the twinkling lights reflecting on the water.

  • Chicago River Night Cruise: $40 per person, 2 hours

Hidden Gems and Local Favorites

When exploring Chicago, don't miss the hidden gems and local favorites. Visit Violet Hour, a stylish speakeasy with innovative cocktails. Explore The 606, an elevated park and trail system converted from an old railroad line. Indulge in authentic Chicago-style hot dogs at Portillo's. Finally, soak in the stunning views of Chicago from the observatory deck of the John Hancock Center.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version