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![Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018ce0f2-bdcd-7954-90a5-c25fb33ec3ce/location455.jpg)
Ultimate 5-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14Magnificent Mile and River Cruises
Morning
Begin your Chicago adventure with a delightful breakfast at The Gage, known for its upscale American cuisine. Afterward, take a leisurely stroll along the iconic Magnificent Mile, home to prestigious boutiques and historic architecture.
Afternoon
Enjoy a classic Chicago experience with the Chicago 45-Minute Family-Friendly Architecture River Cruise. For lunch, head to State and Lake Chicago Tavern for their delicious tavern fare.
Evening
Witness the city's skyline come alive with lights from the 360 Chicago Observation Deck Sip and View Ticket. Cap off the evening with a sumptuous dinner at Lockwood Restaurant & Bar, offering a sophisticated dining experience.
Bedtime
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![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
4.65Magnificent Mile
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![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
Magnificent Mile
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![Visit Chicago 45-Minute Family-Friendly Architecture River Cruise in Chicago](https://cdn.getyourguide.com/img/tour/5e90c47740eaa.jpeg/21.jpg)
4.68Chicago 45-Minute Family-Friendly Architecture River Cruise
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![Visit Chicago 45-Minute Family-Friendly Architecture River Cruise in Chicago](https://cdn.getyourguide.com/img/tour/5e90c47740eaa.jpeg/21.jpg)
Chicago 45-Minute Family-Friendly Architecture River Cruise
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![Visit Chicago 360 Chicago Observation Deck Sip and View Ticket in Chicago](https://cdn.getyourguide.com/img/tour/64931c418a3f9.png/21.jpg)
4.39360 Chicago Observation Deck Sip and View Ticket
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![Visit Chicago 360 Chicago Observation Deck Sip and View Ticket in Chicago](https://cdn.getyourguide.com/img/tour/64931c418a3f9.png/21.jpg)
360 Chicago Observation Deck Sip and View Ticket
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Cultural Immersion and Navy Pier
Morning
Start your day with a visit to the renowned Art Institute of Chicago, where you can enjoy a fast-pass entry. After exploring the art, grab a quick bite at Five Star Bar for a casual yet satisfying meal.
Afternoon
Spend your afternoon at the vibrant Navy Pier, enjoying the various attractions and lakefront views. For a unique experience, consider the Chicago Museum of Ice Cream Entry Ticket. Later, indulge in a gourmet lunch cruise with the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise.
Evening
Dine at The Dearborn, offering a contemporary take on classic American tavern fare. Afterward, take a leisurely walk along the Chicago Riverwalk, admiring the city's architecture and lively atmosphere.
Bedtime
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![Visit Art Institute of Chicago in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/15/da.jpg)
4.61Art Institute of Chicago
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Art Institute of Chicago
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![Visit Navy Pier in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5b/85.jpg)
4.48Navy Pier
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![Visit Navy Pier in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5b/85.jpg)
Navy Pier
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![Visit Chicago Museum of Ice Cream Entry Ticket in Chicago](https://cdn.getyourguide.com/img/tour/0f66132d73a784ca.jpeg/21.jpg)
4.09Chicago Museum of Ice Cream Entry Ticket
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![Visit Chicago Museum of Ice Cream Entry Ticket in Chicago](https://cdn.getyourguide.com/img/tour/0f66132d73a784ca.jpeg/21.jpg)
Chicago Museum of Ice Cream Entry Ticket
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![Visit Chicago Gourmet Brunch, Lunch, or Dinner River Cruise in Chicago](https://cdn.getyourguide.com/img/tour/f2b60b20bebd34c409bd50dee6f07944cfb1230ed4cc2c0a490a52599964464f.jpg/21.jpg)
4.60Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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![Visit Chicago Gourmet Brunch, Lunch, or Dinner River Cruise in Chicago](https://cdn.getyourguide.com/img/tour/f2b60b20bebd34c409bd50dee6f07944cfb1230ed4cc2c0a490a52599964464f.jpg/21.jpg)
Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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![Visit Chicago Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
4.72Chicago Riverwalk
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![Visit Chicago Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
Chicago Riverwalk
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Museum Day and Culinary Delights
Morning
Fuel up for a day of exploration with breakfast at Burger Bar Chicago, known for its mouthwatering burgers. Then, immerse yourself in natural history at the Field Museum of Natural History or opt for a VIP tour.
Afternoon
For lunch, head to The Beetle Bar and Grill for a laid-back dining experience. Afterward, continue your museum journey at the Shedd Aquarium and be amazed by the aquatic wonders.
Evening
Savor the evening at Bar Siena, where you can enjoy a mix of modern and traditional Italian dishes. End the night with a thrilling Chicago Gangsters and Ghosts Guided Walking Tour, exploring the city's darker history.
Bedtime
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![Visit Chicago Field Museum of Natural History Ticket or VIP Tour in Chicago](https://cdn.getyourguide.com/img/tour/a612c084fee2bfaf.jpeg/21.jpg)
4.68Field Museum of Natural History
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![Visit Chicago Field Museum of Natural History Ticket or VIP Tour in Chicago](https://cdn.getyourguide.com/img/tour/a612c084fee2bfaf.jpeg/21.jpg)
Field Museum of Natural History
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![Visit Shedd Aquarium in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
4.75Shedd Aquarium
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![Visit Shedd Aquarium in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
Shedd Aquarium
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![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
4.68Chicago Gangsters and Ghosts Guided Walking Tour
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![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
Chicago Gangsters and Ghosts Guided Walking Tour
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Sky-high Thrills and Local Flavors
Morning
Rise early and catch the sunrise at Skydeck Chicago at Willis Tower (Sears Tower), experiencing the city waking up from a breathtaking vantage point. Afterward, enjoy breakfast at Miller's Pub, a Chicago institution known for its hearty meals.
Afternoon
Spend your afternoon at the Millennium Park, where you can take in the famous Cloud Gate sculpture, also known as "The Bean." For lunch, head to Plymouth Restaurant & Rooftop Bar for a unique dining experience with a view.
Evening
Explore the vibrant neighborhood of Wrigleyville and have dinner at Sweetwater Tavern & Grille. Afterward, catch a live performance at the historic Wrigley Field if there's a game or simply enjoy the lively atmosphere of the area.
Bedtime
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![Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/ed/38/5d.jpg)
4.27Skydeck Chicago at Willis Tower (Sears Tower)
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![Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/ed/38/5d.jpg)
Skydeck Chicago at Willis Tower (Sears Tower)
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![Visit Millennium Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
4.69Millennium Park
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Millennium Park
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![Visit Wrigley Field in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/31/bd/97.jpg)
4.86Wrigley Field
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![Visit Wrigley Field in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/31/bd/97.jpg)
Wrigley Field
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Final Day of Iconic Sights and Farewells
Morning
Enjoy a final breakfast at Emerald Loop Bar & Grill, offering a variety of morning favorites. Then, take a morning stroll at Grant Park, also known as Chicago's "front yard," and visit the majestic Buckingham Fountain.
Afternoon
For your last afternoon in the city, take the Chicago River 1.5-Hour Guided Architecture Cruise to gain a deeper understanding of Chicago's architectural wonders. After the cruise, have a memorable farewell lunch at Fadó Irish Pub, known for its lively atmosphere and authentic Irish dishes.
Evening
Reflect on your Chicago journey over a fine dinner at Gilt Bar, known for its upscale American fare and extensive drink selection. As the night winds down, consider a visit to the historic The Chicago Theatre for a tour or a show, ending your trip with a touch of Chicago's entertainment history.
Bedtime
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![Visit Grant Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/54/eb.jpg)
4.70Grant Park
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![Visit Grant Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/54/eb.jpg)
Grant Park
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![Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/b4b30c0c6eccc80e.jpeg/21.jpg)
4.77Chicago River 1.5-Hour Guided Architecture Cruise
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![Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/b4b30c0c6eccc80e.jpeg/21.jpg)
Chicago River 1.5-Hour Guided Architecture Cruise
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![Visit Chicago Theatre in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
4.71The Chicago Theatre
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![Visit Chicago Theatre in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
The Chicago Theatre
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