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15 Days of Chicago Adventures Itinerary
Last updated: 2024 Jun 30Exploring the Heart of Chicago
Morning
Start your day with a visit to Millennium Park, one of Chicago's most iconic green spaces. Here, you can marvel at the famous Cloud Gate sculpture (often referred to as 'The Bean') and enjoy the serene Lurie Garden. This park is a great way to immerse yourself in the city's vibrant culture and architecture.
Afterward, head over to The Magnificent Mile, a bustling shopping district known for its upscale stores, historic landmarks, and stunning architecture. Take a leisurely stroll down this iconic street and perhaps indulge in some retail therapy or simply enjoy the lively atmosphere.
Afternoon
In the afternoon, embark on Chicago: Art Institute of Chicago Guided Tour. The Art Institute is home to an extensive collection of art from around the world, including famous works by artists like Grant Wood and Georges Seurat. This guided tour will provide you with fascinating insights into the museum's most treasured pieces.
For lunch, stop by Girl & The Goat, a highly-rated restaurant known for its innovative small plates and vibrant atmosphere.
Evening
As evening approaches, make your way to Navy Pier. This popular attraction offers stunning views of Lake Michigan and features various entertainment options such as rides, shops, and restaurants. Don't miss out on taking a ride on the Centennial Wheel for breathtaking views of the city skyline.
For dinner, dine at RPM Steak, an upscale steakhouse offering prime cuts of meat and an elegant dining experience.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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Cultural Immersion in Chicago
Morning
Begin your second day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Ascend to one of the tallest buildings in North America and step out onto The Ledge – glass boxes extending 4.3 feet outside the building – for an exhilarating view from 1,353 feet above ground.
Afterward, explore Chicago Loop, where you'll find architectural marvels like The Rookery Building and historic sites such as Palmer House Hilton.
Afternoon
In the afternoon, join Chicago: Underground Pedway & Downtown Secrets Walking Tour. This tour will take you through Chicago's hidden underground pedestrian pathways while uncovering lesser-known stories about downtown landmarks.
For lunch, head over to Lou Malnati's Pizzeria, renowned for its deep-dish pizza that has become synonymous with Chicago cuisine.
Evening
Conclude your day with a visit to Field Museum, one of the largest natural history museums in the world. Discover fascinating exhibits ranging from ancient Egyptian artifacts to dinosaur skeletons.
Enjoy dinner at The Purple Pig, where you can savor Mediterranean-inspired dishes paired with an extensive wine list.
Bedtime
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.83Chicago Loop
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4.83Chicago Loop
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Architectural Wonders & Scenic Views
Morning
Kick off your third day by visiting 360 Chicago Observation Deck (Formerly John Hancock Observatory). Located on Michigan Avenue within walking distance from Water Tower Place shopping mall; it offers panoramic views over Lake Michigan along with interactive exhibits about local history.
Next up is exploring nearby attractions like Water Tower Place itself which houses numerous shops along side historical landmarks such as Tribune Tower or Wrigley Building both located just few blocks away!
Afternoon
Spend your afternoon enjoying Chicago River: 1.5-Hour Guided Architecture Riverboat Tour. This tour provides insightful commentary about iconic buildings lining both sides river while cruising through heart city’s downtown area! You’ll learn how architects shaped skyline we see today making this must-do activity any visitor interested design history alike!
For lunch try out famous hot dogs at Portillo’s Hot Dogs another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
End third day relaxing walk along picturesque shores Lakefront Trail stretching miles north south providing perfect backdrop sunset stroll before heading back hotel rest up next adventure filled days ahead!
Dinner tonight should be enjoyed Pequod’s Pizza known their caramelized crust deep dish pies beloved locals tourists alike!
Bedtime
Find amazing hotels in Chicago, Illinois.
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.71Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
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4.71Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
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Historical Treasures and Lakeside Fun
Morning
Start your day with a visit to Museum of Science and Industry, one of the largest science museums in the world. This museum offers a plethora of interactive exhibits that will fascinate visitors of all ages. From exploring a World War II submarine to walking through a replica coal mine, there's something for everyone.
Afterward, take a leisurely stroll around the beautiful Hyde Park neighborhood, where the museum is located. The area is known for its historic architecture and vibrant community.
Afternoon
In the afternoon, join Chicago: Lakefront and Museum Campus Segway Tour. This tour provides an exciting way to explore Chicago's stunning lakefront while learning about its rich history. You'll glide past iconic landmarks such as Grant Park, Buckingham Fountain, and Soldier Field.
For lunch, stop by The Promontory, a popular restaurant in Hyde Park known for its wood-fired dishes and relaxed atmosphere.
Evening
As evening approaches, head over to Adler Planetarium, located on the Museum Campus along Lake Michigan. The planetarium offers breathtaking views of the Chicago skyline and fascinating exhibits about space exploration.
For dinner, dine at Gibsons Bar & Steakhouse, an iconic Chicago steakhouse offering prime cuts of meat and classic American fare.
Bedtime
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.93Chicago: Lakefront and Museum Campus Segway Tour
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4.93Chicago: Lakefront and Museum Campus Segway Tour
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Architectural Marvels & Urban Adventures
Morning
Begin your day with a visit to Rookery Building, one of Chicago's most famous architectural landmarks designed by Daniel Burnham and John Root. The building's stunning lobby was later remodeled by Frank Lloyd Wright, making it a must-see for architecture enthusiasts.
Next up is exploring nearby attractions like Marina City, an iconic twin-tower complex that has become synonymous with Chicago's skyline.
Afternoon
In the afternoon, embark on Chicago: Bikes Bites and Brews Biking Tour. This tour combines cycling with culinary delights as you pedal through various neighborhoods sampling local foods such as deep-dish pizza hot dogs craft beers! It’s perfect way experience city’s diverse culture cuisine while staying active!
For lunch try out famous Italian beef sandwiches at Al’s Beef another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
Conclude your day with a visit to United Center, home to both NBA’s Bulls NHL’s Blackhawks teams! Even if there isn’t game scheduled during stay still worth checking out arena taking guided tour learn more about its history significance sports fans alike!
Enjoy dinner at Girl & The Goat, where you can savor innovative small plates crafted by celebrity chef Stephanie Izard paired with an extensive wine list.
Bedtime
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4.73Rookery Building
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4.73Rookery Building
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4.84Marina City
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4.84Marina City
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Cultural Gems & Scenic Cruises
Morning
Kick off your sixth day by visiting Chicago Cultural Center. This stunning building hosts free art exhibitions concerts performances throughout year making it great place immerse yourself city’s vibrant arts scene! Don’t miss chance see world-renowned Tiffany stained glass dome located inside too!
Next up is exploring nearby attractions like Millennium Park itself which houses numerous sculptures gardens along side historical landmarks such as Tribune Tower or Wrigley Building both located just few blocks away!
Afternoon
Spend your afternoon enjoying Chicago: 1.5-Hour Scenic Sunset Lake Cruise. This tour provides insightful commentary about iconic buildings lining both sides river while cruising through heart city’s downtown area! You’ll learn how architects shaped skyline we see today making this must-do activity any visitor interested design history alike!
For lunch try out famous hot dogs at Portillo’s Hot Dogs another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
End sixth day relaxing walk along picturesque shores Lakefront Trail stretching miles north south providing perfect backdrop sunset stroll before heading back hotel rest up next adventure filled days ahead!
Dinner tonight should be enjoyed Pequod’s Pizza known their caramelized crust deep dish pies beloved locals tourists alike!
Bedtime
Find amazing hotels in Chicago, Illinois.
4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.61Chicago: 1.5-Hour Scenic Sunset Lake Cruise
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4.61Chicago: 1.5-Hour Scenic Sunset Lake Cruise
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Urban Exploration and Hidden Gems
Morning
Start your day with a visit to Chicago Pedway. This network of underground tunnels and overhead bridges connects many of the city's buildings, offering a unique way to explore Chicago's downtown area. The Pedway is especially useful during inclement weather, providing a sheltered route through the city.
Afterward, head over to Chicago Board of Trade Building, an iconic Art Deco skyscraper that has been a central hub for commodities trading since 1930. Take a guided tour to learn about its history and architectural significance.
Afternoon
In the afternoon, join Chicago: Underground Pedway & Downtown Secrets Walking Tour. This tour will take you through Chicago's hidden underground pedestrian pathways while uncovering lesser-known stories about downtown landmarks.
For lunch, stop by The Gage, a popular gastropub known for its hearty American fare and lively atmosphere.
Evening
As evening approaches, make your way to House of Blues. This iconic music venue hosts live performances from both local and international artists across various genres. Enjoy an evening filled with great music and vibrant energy.
For dinner, dine at Siena Tavern, an Italian restaurant offering delicious pasta dishes and wood-fired pizzas.
Bedtime
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4.94Chicago Pedway
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4.94Chicago Pedway
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4.87Chicago Board of Trade Building
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4.87Chicago Board of Trade Building
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Architectural Wonders & Scenic Views
Morning
Kick off your eighth day by visiting 360 Chicago Observation Deck (Formerly John Hancock Observatory). Located on Michigan Avenue within walking distance from Water Tower Place shopping mall; it offers panoramic views over Lake Michigan along with interactive exhibits about local history.
Next up is exploring nearby attractions like Water Tower Place itself which houses numerous shops along side historical landmarks such as Tribune Tower or Wrigley Building both located just few blocks away!
Afternoon
Spend your afternoon enjoying Chicago River: 1.5-Hour Guided Architecture Riverboat Tour. This tour provides insightful commentary about iconic buildings lining both sides river while cruising through heart city’s downtown area! You’ll learn how architects shaped skyline we see today making this must-do activity any visitor interested design history alike!
For lunch try out famous hot dogs at Portillo’s Hot Dogs another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
End eighth day relaxing walk along picturesque shores Lakefront Trail stretching miles north south providing perfect backdrop sunset stroll before heading back hotel rest up next adventure filled days ahead!
Dinner tonight should be enjoyed Pequod’s Pizza known their caramelized crust deep dish pies beloved locals tourists alike!
Bedtime
Find amazing hotels in Chicago, Illinois.
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
Book Now
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
Book Now
4.71Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
Book Now
4.71Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
Book Now
Cultural Immersion & Lakeside Fun
Morning
Begin your ninth day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Ascend to one of the tallest buildings in North America and step out onto The Ledge – glass boxes extending 4.3 feet outside the building – for an exhilarating view from 1,353 feet above ground.
Afterward explore nearby attractions like Millennium Park itself which houses numerous sculptures gardens along side historical landmarks such as Tribune Tower or Wrigley Building both located just few blocks away!
Afternoon
In afternoon join Chicago: Bikes Bites Brews Biking Tour combining cycling culinary delights pedaling through various neighborhoods sampling local foods such deep-dish pizza hot dogs craft beers perfect way experience city’s diverse culture cuisine while staying active!
For lunch try out famous Italian beef sandwiches Al’s Beef another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
Conclude ninth day visiting Field Museum one largest natural history museums world discovering fascinating exhibits ranging ancient Egyptian artifacts dinosaur skeletons enjoy dinner Purple Pig savor Mediterranean-inspired dishes paired extensive wine list.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.87Chicago: Bikes Bites Brews Biking Tour
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4.87Chicago: Bikes Bites Brews Biking Tour
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Artistic Explorations and River Adventures
Morning
Begin your tenth day with a visit to Art Institute of Chicago. This world-renowned museum houses an extensive collection of art from various periods and regions, including iconic works like Grant Wood's 'American Gothic' and Georges Seurat's 'A Sunday on La Grande Jatte'. Spend your morning exploring the diverse exhibits and soaking in the artistic atmosphere.
Afterward, take a leisurely stroll through nearby Grant Park, often referred to as 'Chicago's front yard'. This large urban park offers beautiful gardens, sculptures, and fountains.
Afternoon
In the afternoon, embark on Chicago River: 1.5-Hour Guided Architecture Riverboat Tour. This tour provides insightful commentary about the iconic buildings lining both sides of the river while cruising through the heart of the city’s downtown area. You’ll learn how architects shaped the skyline we see today, making this a must-do activity for any visitor interested in design and history alike!
For lunch, head over to The Dearborn, a popular American tavern known for its classic dishes and welcoming atmosphere.
Evening
As evening approaches, make your way to Chicago Theatre. This historic venue hosts a variety of performances ranging from concerts to Broadway shows. Enjoy an evening filled with entertainment in one of Chicago's most iconic theaters.
For dinner, dine at Bavette's Bar & Boeuf, an upscale steakhouse offering prime cuts of meat and an elegant dining experience.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.71Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
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4.71Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
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Historical Insights & Lakeside Leisure
Morning
Start your eleventh day with a visit to Field Museum, one of the largest natural history museums in the world. Discover fascinating exhibits ranging from ancient Egyptian artifacts to dinosaur skeletons. The museum’s extensive collection will captivate visitors of all ages.
Afterward explore nearby attractions like Millennium Park itself which houses numerous sculptures gardens along side historical landmarks such as Tribune Tower or Wrigley Building both located just few blocks away!
Afternoon
In afternoon join Chicago: Bikes Bites Brews Biking Tour combining cycling culinary delights pedaling through various neighborhoods sampling local foods such deep-dish pizza hot dogs craft beers perfect way experience city’s diverse culture cuisine while staying active!
For lunch try out famous Italian beef sandwiches Al’s Beef another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
Conclude eleventh day visiting Field Museum one largest natural history museums world discovering fascinating exhibits ranging ancient Egyptian artifacts dinosaur skeletons enjoy dinner Purple Pig savor Mediterranean-inspired dishes paired extensive wine list.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.56Field Museum
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4.56Field Museum
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4.87Chicago: Bikes Bites Brews Biking Tour
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4.87Chicago: Bikes Bites Brews Biking Tour
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Cultural Immersion & Lakeside Fun
Morning
Begin your twelfth day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Ascend to one of the tallest buildings in North America and step out onto The Ledge – glass boxes extending 4.3 feet outside the building – for an exhilarating view from 1,353 feet above ground.
Afterward explore nearby attractions like Millennium Park itself which houses numerous sculptures gardens along side historical landmarks such as Tribune Tower or Wrigley Building both located just few blocks away!
Afternoon
In afternoon join Chicago: Bikes Bites Brews Biking Tour combining cycling culinary delights pedaling through various neighborhoods sampling local foods such deep-dish pizza hot dogs craft beers perfect way experience city’s diverse culture cuisine while staying active!
For lunch try out famous Italian beef sandwiches Al’s Beef another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
Conclude twelfth day visiting Field Museum one largest natural history museums world discovering fascinating exhibits ranging ancient Egyptian artifacts dinosaur skeletons enjoy dinner Purple Pig savor Mediterranean-inspired dishes paired extensive wine list.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.87Chicago: Bikes Bites Brews Biking Tour
Book Now
4.87Chicago: Bikes Bites Brews Biking Tour
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Historical Landmarks and River Cruises
Morning
Start your thirteenth day with a visit to Tribune Tower. This neo-Gothic skyscraper is one of Chicago's most famous landmarks, known for its stunning architecture and the fragments of historic buildings from around the world embedded in its walls. Take some time to explore this architectural marvel and learn about its rich history.
Afterward, head over to Wrigley Building, another iconic structure located just across the street. This building's white terra cotta facade and clock tower make it a must-see for any visitor.
Afternoon
In the afternoon, join Chicago: Architecture Boat Tour with Drinks. This tour provides insightful commentary about the iconic buildings lining both sides of the river while you enjoy a refreshing drink. It's a relaxing way to learn about Chicago's architectural heritage while taking in stunning views of the city.
For lunch, stop by The Purple Pig, a popular restaurant known for its Mediterranean-inspired dishes and extensive wine list.
Evening
As evening approaches, make your way to Second City. This legendary comedy club has launched the careers of many famous comedians and offers hilarious performances that will leave you in stitches. Enjoy an evening filled with laughter and entertainment.
For dinner, dine at RPM Italian, an upscale Italian restaurant offering delicious pasta dishes and an elegant dining experience.
Bedtime
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4.61Tribune Tower
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4.61Tribune Tower
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4.39Wrigley Building
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4.39Wrigley Building
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Cultural Immersion & Scenic Views
Morning
Lincoln Park & Zoo is your first stop on day fourteen. Located in one of Chicago's most picturesque neighborhoods, this free zoo is home to a wide variety of animals from around the world. Spend your morning exploring the exhibits and enjoying the beautiful park surroundings.
Afterward, take a leisurely stroll through Lincoln Park itself, which offers scenic walking paths, gardens, and stunning views of Lake Michigan.
Afternoon
Chicago: Gangsters and Ghosts Guided Walking Tour awaits you in the afternoon. This tour delves into Chicago's notorious past, exploring stories of infamous gangsters like Al Capone as well as haunted locations throughout downtown. It's an intriguing way to learn about the city's darker history.
For lunch, head over to Lou Malnati's Pizzeria, renowned for its deep-dish pizza that has become synonymous with Chicago cuisine.
Evening
Chicago Riverwalk is perfect for an evening stroll. This pedestrian-friendly path along the Chicago River offers beautiful views of the city skyline and numerous dining options along its route. Take some time to relax by the water and soak in the vibrant atmosphere.
Enjoy dinner at The Gage, where you can savor hearty American fare paired with craft beers or cocktails.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.68Chicago: Gangsters and Ghosts Guided Walking Tour
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4.68Chicago: Gangsters and Ghosts Guided Walking Tour
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Final Day Adventures & Farewell
Morning
Adler Planetarium kicks off your final day in Chicago. Located on Museum Campus along Lake Michigan; it offers breathtaking views city skyline fascinating exhibits about space exploration making great place start last adventure-filled day!
Afterward explore nearby attractions like Shedd Aquarium Field Museum both located within walking distance providing perfect opportunity immerse yourself more cultural experiences before departure!
Afternoon
Chicago: Prohibition Speakeasies Bus Tour or Walking Tour takes center stage afternoon! Learn all about city’s Prohibition-era history visiting hidden speakeasies hearing tales bootleggers law enforcement efforts combat illegal alcohol trade during roaring twenties!
For lunch try out famous hot dogs Portillo’s Hot Dogs another staple local cuisine offering variety toppings sure satisfy taste buds!
Evening
End fifteenth day relaxing walk along picturesque shores Lakefront Trail stretching miles north south providing perfect backdrop sunset stroll before heading back hotel rest up next adventure filled days ahead!
Dinner tonight should be enjoyed Pequod’s Pizza known their caramelized crust deep dish pies beloved locals tourists alike!
Bedtime
Find amazing hotels in Chicago, Illinois.
4.61Adler Planetarium
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4.61Adler Planetarium
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4.90Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
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4.90Chicago: Prohibition Speakeasies Bus Tour or Walking Tour
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