15 Must-See Tours In Chicago: Insider Tips From A Local!

Welcome to the Windy City! As a local, I’m here to share my insider tips on the 15 must-see tours in Chicago. From the iconic skyline to the hidden gems, I’m sure you’ll find something to love in this vibrant city. So let’s get started!

1. Chicago Skydeck + “The Ledge” Experience Ticket

Source: Chicago Skydeck

If you’re looking for a unique experience that will take your breath away, then the Chicago Skydeck + \The Ledge\ Experience is the perfect destination for you! From the 103rd floor of the Willis Tower, you’ll get a stunning view of the city of Chicago and Lake Michigan. Plus, you’ll get to stand on the glass-floored balconies of \The Ledge\ for an unforgettable experience!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Chance of Rain
April	Cool, Chance of Rain
May	Warm, Chance of Rain
June	Warm, Chance of Rain
July	Hot, Chance of Rain
August	Hot, Chance of Rain
September	Warm, Chance of Rain
October	Cool, Chance of Rain
November	Cool, Chance of Rain
December	Cold, Snowy

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Randolph/Wabash station. From there, take the Chicago Transit Authority (CTA) Blue Line to the Clark/Lake station. From there, take the CTA bus #151 to the Skydeck.
Bus	Take the CTA bus #151 to the Skydeck.
Flight	Fly into Chicago O’Hare International Airport (ORD). From there, take the CTA Blue Line to the Clark/Lake station. From there, take the CTA bus #151 to the Skydeck.

Local tips:

• Plan your visit to the Skydeck in advance to avoid long lines.
• Arrive early to get the best views and avoid the crowds.
• Bring a camera to capture the amazing views.
• Dress appropriately for the weather.
• Be aware of the height and take safety precautions.
• Take advantage of the audio tour to learn more about the city.
• Purchase tickets online to save time and money.
• Check out the interactive exhibits and activities.
• Visit the Ledge for a unique perspective of the city.

2. Chicago River Architecture Cruise

Source: Chicago River Architecture Cruise

If you’re looking for a unique way to explore the stunning architecture of Chicago, then the Chicago River Architecture Cruise is the perfect choice! From the iconic Willis Tower to the historic Wrigley Building, you’ll get an up-close and personal view of the city’s most iconic landmarks. Plus, you’ll learn about the history and culture of the city from the knowledgeable tour guides. So come join us on the Chicago River Architecture Cruise and experience the beauty of the Windy City!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Chance of Rain
April	Cool, Chance of Rain
May	Warm, Chance of Rain
June	Warm, Chance of Rain
July	Hot, Chance of Rain
August	Hot, Chance of Rain
September	Warm, Chance of Rain
October	Cool, Chance of Rain
November	Cool, Chance of Rain
December	Cold, Chance of Snow

Best time to visit the Chicago River Architecture Cruise is during the months of May through September when the weather is warm and there is a chance of rain.

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to Museum Campus/11th Street Station. From there, take the #146 Inner Drive/Michigan Express bus to the Michigan Avenue/Wacker Drive stop.
Bus	Take the #146 Inner Drive/Michigan Express bus to the Michigan Avenue/Wacker Drive stop.
Flight	Fly into Chicago O’Hare International Airport (ORD). From there, take the CTA Blue Line train to the Clark/Lake station. From there, take the #146 Inner Drive/Michigan Express bus to the Michigan Avenue/Wacker Drive stop.

Local tips:

• Bring a camera to capture the amazing views of the city skyline.
• Wear comfortable shoes as you will be standing for a while.
• Bring a light jacket or sweater as the temperature can change quickly.
• Check the weather forecast before you go.
• Arrive early to get a good spot on the boat.
• Bring a hat and sunscreen to protect yourself from the sun.
• Bring a snack and water to stay hydrated.
• Be prepared to learn about the history of the city.
• Be aware of the safety rules and regulations of the boat.

3. Wicker Park Walking Food Tour

Source: Wicker Park Food Tour

Come explore the vibrant and eclectic Wicker Park neighborhood on a walking food tour! Sample delicious cuisine from local restaurants, learn about the history of the area, and discover why Wicker Park is one of the most popular neighborhoods in the United States.

Best time to visit:

Month	Best Time to Visit	Weather
January	Late January	Cold, Snowy
February	Early February	Cold, Snowy
March	Late March	Cool, Rainy
April	Early April	Cool, Rainy
May	Late May	Warm, Sunny
June	Early June	Warm, Sunny
July	Late July	Hot, Humid
August	Early August	Hot, Humid
September	Late September	Cool, Rainy
October	Early October	Cool, Rainy
November	Late November	Cold, Snowy
December	Early December	Cold, Snowy

How to reach:

Mode of Transport	Instructions
Train	Take the Blue Line train to the Damen stop. The tour starts at the Damen stop.
Bus	Take the 50 Damen bus to the Damen stop. The tour starts at the Damen stop.
Flight	Fly into Chicago O’Hare International Airport. Take the Blue Line train to the Damen stop. The tour starts at the Damen stop.

Local tips:

• Bring comfortable shoes and clothing as you will be walking for the duration of the tour.
• Bring a camera to capture the unique sights and flavors of the area.
• Be prepared to try a variety of different foods, as the tour will feature a variety of cuisines.
• Be sure to bring cash, as some of the vendors may not accept credit cards.
• Be sure to stay hydrated, as the tour will last several hours.
• Be sure to ask questions and interact with the tour guide to get the most out of the experience.

4. 90-Minute Mob and Crime Bus Tour

Source: Mob And Crime Bus Tour

Experience the thrill of a lifetime on the 90-Minute Mob and Crime Bus Tour! Take a journey through the dark side of the United States and explore the history of organized crime and the mob. From the infamous Al Capone to the modern-day mobsters, you’ll get an up-close and personal look at the criminal underworld. So come join us and discover the secrets of the mob and crime in the United States!

Best time to visit:

Month	Weather
January	Cold
February	Cold
March	Cool
April	Mild
May	Warm
June	Warm
July	Hot
August	Hot
September	Mild
October	Cool
November	Cool
December	Cold

Best time to visit the 90-Minute Mob and Crime Bus Tour in the United States is from April to August when the weather is mild to hot.

How to reach:

Mode of Transport	How to Reach
Train	The 90-Minute Mob and Crime Bus Tour is not accessible by train.
Bus	The 90-Minute Mob and Crime Bus Tour is accessible by bus. You can take a bus from the nearest bus station to the tour’s starting point.
Flight	The 90-Minute Mob and Crime Bus Tour is not accessible by flight. You will need to take a bus or a car to the tour’s starting point.

Local tips:

• Be aware of your surroundings and stay alert at all times.
• Be aware of the local laws and regulations.
• Bring a map or GPS device to help you navigate the area.
• Bring a camera to capture the sights and sounds of the tour.
• Dress appropriately for the weather and wear comfortable shoes.
• Bring snacks and water to stay hydrated and energized.
• Be respectful of the local culture and customs.
• Be prepared for unexpected delays or changes in the tour.
• Be prepared to pay for any additional costs associated with the tour.

5. Treasures of Chicago’s Golden Age: 90-Minute Walking Tour

Source: Palmer House Hotel

If you’re looking for a unique way to explore the history and culture of Chicago, then the Treasures of Chicago’s Golden Age: 90-Minute Walking Tour is the perfect choice! This tour takes you through the city’s most iconic landmarks and neighborhoods, giving you a glimpse into the city’s past and present. From the grandeur of the Chicago Theatre to the hustle and bustle of the Loop, you’ll get to experience the best of what Chicago has to offer. So come join us and discover the treasures of Chicago’s golden age!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Rainy
April	Cool, Rainy
May	Warm, Sunny
June	Warm, Sunny
July	Hot, Humid
August	Hot, Humid
September	Warm, Sunny
October	Cool, Rainy
November	Cool, Rainy
December	Cold, Snowy

Best time to visit Treasures of Chicago’s Golden Age: 90-Minute Walking Tour is during the months of May to September when the weather is warm and sunny.

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Randolph/Wabash station. The tour starts at the corner of Randolph and Wabash.
Bus	Take the CTA bus #3, #4, #14, #20, #56, #60, #124, #157, or #173 to the Randolph/Wabash station. The tour starts at the corner of Randolph and Wabash.
Flight	Fly into Chicago O’Hare International Airport (ORD). Take the CTA Blue Line train to the Randolph/Wabash station. The tour starts at the corner of Randolph and Wabash.

Local tips:

• Wear comfortable shoes as the tour is 90 minutes long and involves a lot of walking.
• Bring an umbrella or a raincoat in case of rain.
• Bring a camera to capture the beautiful sights of the city.
• Be prepared to learn about the history of Chicago and its golden age.
• Be sure to ask questions and interact with the tour guide.
• Be sure to stay hydrated and bring a bottle of water.
• Be sure to wear sunscreen and a hat to protect yourself from the sun.

6. Chicago Secret Food Tour

Source: Chicago: Secret Food Tour

Welcome to the Chicago Secret Food Tour! Come explore the hidden gems of the Windy City and discover the unique flavors of Chicago’s diverse culinary scene. From classic Chicago-style hot dogs to deep-dish pizza, you’ll get to experience the best of the city’s food culture. So come join us and let your taste buds take you on a journey through the city’s secret food spots!

Best time to visit:

Month	Best Time to Visit	Weather
March	Early March	Average temperature of 40°F (4°C)
April	Mid April	Average temperature of 50°F (10°C)
May	Late May	Average temperature of 60°F (15°C)
June	Early June	Average temperature of 70°F (21°C)
July	Mid July	Average temperature of 80°F (26°C)
August	Late August	Average temperature of 80°F (26°C)
September	Early September	Average temperature of 70°F (21°C)
October	Mid October	Average temperature of 60°F (15°C)
November	Late November	Average temperature of 50°F (10°C)
December	Early December	Average temperature of 40°F (4°C)

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Randolph Street Station. The tour departs from the Randolph Street Station.
Bus	Take the CTA bus #29 to the Randolph Street Station. The tour departs from the Randolph Street Station.
Flight	Fly into Chicago O’Hare International Airport (ORD). Take the CTA Blue Line train to the Randolph Street Station. The tour departs from the Randolph Street Station.

Local tips:

• Visit the Chicago Riverwalk for a great view of the city.
• Check out the Chicago Cultural Center for free art and music events.
• Take a stroll through Millennium Park and take in the beauty of the city.
• Visit the Art Institute of Chicago for a great collection of art.
• Explore the city’s many neighborhoods for unique restaurants and shops.
• Visit the Navy Pier for a great view of the lakefront.
• Take a tour of the Chicago Architecture Foundation for a great look at the city’s history.
• Visit the Field Museum for a great look at the city’s natural history.
• Check out the Shedd Aquarium for a great look at the city’s aquatic life.
• Visit the Lincoln Park Zoo for a great look at the city’s wildlife.

7. Loop Interior Architecture: 2-Hour Walking Tour

Source: Loop Interior Architecture Walking Tour

Are you looking for a unique and exciting way to explore the United States? Look no further than the Loop Interior Architecture: 2-Hour Walking Tour! This tour offers a unique opportunity to explore the stunning architecture of the Loop, one of the most iconic neighborhoods in the United States. From historic buildings to modern skyscrapers, this tour will give you an up-close look at the beauty of the city. So come join us and experience the beauty of the Loop for yourself!

Best time to visit:

Month	Best Time to Visit	Weather
January	Late January	Cold, with temperatures ranging from the mid-30s to the mid-50s
February	Early February	Cold, with temperatures ranging from the mid-30s to the mid-50s
March	Late March	Cool, with temperatures ranging from the mid-40s to the mid-60s
April	Early April	Cool, with temperatures ranging from the mid-50s to the mid-70s
May	Late May	Warm, with temperatures ranging from the mid-60s to the mid-80s
June	Early June	Warm, with temperatures ranging from the mid-70s to the mid-90s
July	Late July	Hot, with temperatures ranging from the mid-70s to the mid-90s
August	Early August	Hot, with temperatures ranging from the mid-70s to the mid-90s
September	Late September	Warm, with temperatures ranging from the mid-60s to the mid-80s
October	Early October	Cool, with temperatures ranging from the mid-50s to the mid-70s
November	Late November	Cool, with temperatures ranging from the mid-40s to the mid-60s
December	Early December	Cold, with temperatures ranging from the mid-30s to the mid-50s

How to reach:

Mode of Transport	Instructions
Train	Take the train to the nearest station to Loop Interior Architecture: 2-Hour Walking Tour. Check the train schedule for the nearest station.
Bus	Take the bus to the nearest bus stop to Loop Interior Architecture: 2-Hour Walking Tour. Check the bus schedule for the nearest bus stop.
Flight	Take a flight to the nearest airport to Loop Interior Architecture: 2-Hour Walking Tour. Check the flight schedule for the nearest airport.

Local tips:

• Wear comfortable shoes as you will be walking for two hours.
• Bring a camera to capture the amazing architecture.
• Bring a bottle of water to stay hydrated.
• Be prepared to learn about the history of the area.
• Be sure to ask questions and interact with the tour guide.
• Be aware of your surroundings and stay safe.

8. Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe

Source: Chicago Hop-on Hop-off

Experience the beauty of Chicago with a Hop-on-Hop-off Bus Tour! From the classic to the premium and deluxe packages, you’ll get to explore the city’s iconic landmarks, vibrant neighborhoods, and stunning skyline. With convenient stops and knowledgeable guides, you’ll get the most out of your visit to the Windy City. So hop on and explore Chicago today!

Best time to visit:

Month	Best Time to Visit	Weather
January	Late January	Cold, Snowy
February	Early February	Cold, Snowy
March	Late March	Cool, Rainy
April	Early April	Cool, Rainy
May	Late May	Warm, Sunny
June	Early June	Warm, Sunny
July	Late July	Hot, Humid
August	Early August	Hot, Humid
September	Late September	Cool, Rainy
October	Early October	Cool, Rainy
November	Late November	Cold, Snowy
December	Early December	Cold, Snowy

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Museum Campus/11th Street Station. From there, take the #146 bus to the Chicago Hop-on-Hop-off Bus Tour.
Bus	Take the #146 bus from any downtown Chicago bus stop to the Chicago Hop-on-Hop-off Bus Tour.
Flight	Fly into Chicago O’Hare International Airport (ORD). From there, take the CTA Blue Line to the Clark/Lake Station. From there, take the #146 bus to the Chicago Hop-on-Hop-off Bus Tour.

Local tips:

• Take advantage of the Hop-on-Hop-off Bus Tour’s flexibility and hop off at any of the stops to explore the city.
• Be sure to check out the city’s iconic attractions, such as the Willis Tower, Navy Pier, and Millennium Park.
• Take advantage of the audio tour to learn more about the city’s history and culture.
• Be sure to bring a camera to capture the beautiful views of the city.
• Be sure to dress appropriately for the weather, as the tour is outdoors.
• Be sure to wear comfortable shoes, as you will be doing a lot of walking.
• Be sure to bring a water bottle and snacks to keep you energized throughout the tour.
• Be sure to check the tour’s website for any discounts or special offers.

9. Gourmet Brunch, Lunch, or Dinner River Cruise

Source: Gourmet Brunch, Lunch, or Dinner River Cruise

Experience the beauty of the United States from a unique perspective with a Gourmet Brunch, Lunch, or Dinner River Cruise! Enjoy a delicious meal while taking in the stunning views of the river and its surrounding landscape. With a variety of options to choose from, you’re sure to find the perfect cruise for you and your loved ones. So come aboard and let us show you the best of the United States from the comfort of a river cruise!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Rainy
April	Cool, Rainy
May	Warm, Sunny
June	Warm, Sunny
July	Hot, Humid
August	Hot, Humid
September	Warm, Sunny
October	Cool, Rainy
November	Cool, Rainy
December	Cold, Snowy

Best time to visit Gourmet Brunch, Lunch, or Dinner River Cruise in United States is during the months of May to September when the weather is warm and sunny.

How to reach:

Mode of Transport	How to Reach
Train	Check the local train routes and schedules to reach the nearest station to the Gourmet Brunch, Lunch, or Dinner River Cruise.
Bus	Check the local bus routes and schedules to reach the nearest bus stop to the Gourmet Brunch, Lunch, or Dinner River Cruise.
Flight	Check the local airports and flight schedules to reach the nearest airport to the Gourmet Brunch, Lunch, or Dinner River Cruise.

Local tips:

• Check the cruise company’s website for the latest information on the cruise route, departure times, and cost.
• Book your tickets in advance to avoid disappointment.
• Check the dress code for the cruise and dress accordingly.
• Bring a camera to capture the beautiful views of the river.
• Bring a light jacket or sweater in case it gets chilly on the cruise.
• Bring your own snacks and drinks if you want to save money.
• Be sure to tip the staff for their excellent service.
• Be aware of the safety regulations and follow them.
• Be sure to check the weather forecast before you go.
• Be sure to check the cruise company’s website for any special offers or discounts.

10. Chicago’s Modern Skyscrapers Guided Walking Tour

Source: Chicago Skyscrapers

If you’re looking for a unique way to explore the Windy City, then look no further than Chicago’s Modern Skyscrapers Guided Walking Tour! This tour offers a unique perspective on the city’s iconic skyline, with a knowledgeable guide to show you the best of the city’s modern architecture. From the Willis Tower to the John Hancock Center, you’ll get an up-close look at some of the most impressive skyscrapers in the world. So come join us and experience the beauty of Chicago’s modern skyline!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Chance of Rain
April	Cool, Chance of Rain
May	Warm, Chance of Rain
June	Warm, Chance of Rain
July	Hot, Chance of Rain
August	Hot, Chance of Rain
September	Warm, Chance of Rain
October	Cool, Chance of Rain
November	Cool, Chance of Rain
December	Cold, Snowy

Best time to visit Chicago’s Modern Skyscrapers Guided Walking Tour is during the months of May to September when the weather is warm and there is a chance of rain.

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Randolph/Wabash station. The tour starts at the Chicago Cultural Center, which is a short walk from the station.
Bus	Take the CTA bus #3 King Drive to the Randolph/Wabash station. The tour starts at the Chicago Cultural Center, which is a short walk from the station.
Flight	Fly into Chicago O’Hare International Airport (ORD). Take the CTA Blue Line train to the Randolph/Wabash station. The tour starts at the Chicago Cultural Center, which is a short walk from the station.

Local tips:

• Wear comfortable shoes as the tour is a walking tour.
• Bring a camera to capture the amazing views of the city.
• Be prepared to walk for a few hours.
• Check the weather forecast before the tour.
• Bring a bottle of water and snacks.
• Be aware of your surroundings and stay safe.
• Be respectful of the local culture and customs.
• Be prepared to ask questions and learn about the city.

11. Private Helicopter Flight

Source: Private Helicopter Flight

Experience the thrill of a lifetime with a private helicopter flight in the United States! Soar through the skies and take in the breathtaking views of the country’s most iconic landmarks. From the Grand Canyon to the Statue of Liberty, you’ll get a unique perspective of the country that you won’t find anywhere else. So come and join us for an unforgettable journey!

Best time to visit:

Month	Weather
January	Cold, dry weather with occasional snow
February	Cold, dry weather with occasional snow
March	Cool, dry weather with occasional rain
April	Cool, dry weather with occasional rain
May	Warm, dry weather with occasional rain
June	Warm, dry weather with occasional rain
July	Hot, dry weather with occasional thunderstorms
August	Hot, dry weather with occasional thunderstorms
September	Warm, dry weather with occasional rain
October	Cool, dry weather with occasional rain
November	Cold, dry weather with occasional snow
December	Cold, dry weather with occasional snow

The best time to visit the United States for a private helicopter flight is during the months of May through August when the weather is warm and dry with occasional rain or thunderstorms.

How to reach:

Mode of Transport	How to Reach
Train	Most major cities in the United States have train stations that offer direct service to the nearest airport. From there, you can take a private helicopter flight to your destination.
Bus	Many cities in the United States offer bus services to the nearest airport. From there, you can take a private helicopter flight to your destination.
Flight	You can book a direct flight to the nearest airport to your destination. From there, you can take a private helicopter flight to your destination.

Local tips:

• Check the local regulations and laws for private helicopter flights in the United States.
• Make sure to book a certified and experienced pilot.
• Check the weather conditions before the flight.
• Check the safety record of the helicopter.
• Check the insurance coverage of the helicopter.
• Check the maintenance records of the helicopter.
• Check the availability of the helicopter.
• Check the cost of the flight.
• Check the availability of the landing sites.
• Check the availability of the refueling sites.
• Check the availability of the navigation aids.
• Check the availability of the communication systems.
• Check the availability of the emergency services.
• Check the availability of the medical services.
• Check the availability of the rescue services.

12. Navy Pier Centennial Wheel

Source: Navy Pier

If you’re looking for a unique experience that will take your breath away, then the Navy Pier Centennial Wheel in the United States is the perfect place for you! With stunning views of the Chicago skyline, Lake Michigan, and the surrounding area, the Navy Pier Centennial Wheel is a must-see destination for anyone looking for a memorable experience.

Best time to visit:

Month	Best Time to Visit	Weather
January	Late Afternoon	Cold, Snowy
February	Late Afternoon	Cold, Snowy
March	Late Afternoon	Cool, Windy
April	Late Afternoon	Cool, Windy
May	Late Afternoon	Warm, Sunny
June	Late Afternoon	Warm, Sunny
July	Late Afternoon	Hot, Humid
August	Late Afternoon	Hot, Humid
September	Late Afternoon	Warm, Sunny
October	Late Afternoon	Cool, Windy
November	Late Afternoon	Cool, Windy
December	Late Afternoon	Cold, Snowy

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Randolph/Michigan Avenue station. From there, take the Navy Pier Trolley to the Navy Pier Centennial Wheel.
Bus	Take the CTA bus #29 to the Navy Pier. From there, take the Navy Pier Trolley to the Navy Pier Centennial Wheel.
Flight	Fly into Chicago O’Hare International Airport. From there, take the CTA Blue Line to the Clark/Lake station. From there, take the CTA bus #29 to the Navy Pier. From there, take the Navy Pier Trolley to the Navy Pier Centennial Wheel.

Local tips:

• Take the time to explore the Navy Pier Centennial Wheel and all the attractions it has to offer.
• Be sure to check out the amazing views of the city from the top of the wheel.
• Take advantage of the discounts and special offers available for the wheel.
• Be sure to dress appropriately for the weather and wear comfortable shoes.
• Bring a camera to capture the amazing views from the top of the wheel.
• Be sure to check out the other attractions at Navy Pier such as the Children’s Museum, the Chicago Shakespeare Theater, and the Crystal Gardens.
• Be sure to check out the restaurants and shops at Navy Pier.
• Be sure to check out the fireworks displays at Navy Pier.
• Be sure to check out the live music and entertainment at Navy Pier.

13. Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour

Source: Bobby’s Bike Hike Chicago

Come explore the beautiful Lakefront Neighborhoods of Chicago with Bobby’s Bike Hike! From the iconic Navy Pier to the stunning architecture of the Gold Coast, this tour is the perfect way to experience the best of the Windy City. With knowledgeable guides, comfortable bikes, and breathtaking views, you won’t want to miss this one-of-a-kind adventure!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Chance of Rain
April	Cool, Chance of Rain
May	Warm, Chance of Rain
June	Warm, Chance of Rain
July	Hot, Chance of Rain
August	Hot, Chance of Rain
September	Warm, Chance of Rain
October	Cool, Chance of Rain
November	Cool, Chance of Rain
December	Cold, Chance of Snow

Best time to visit Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour is during the months of May to September when the weather is warm and there is a chance of rain.

How to reach:

Local tips:

• Bring a camera to capture the beautiful views of the lakefront neighborhoods.
• Wear comfortable shoes and clothing as you will be walking and biking for a few hours.
• Bring a water bottle and snacks to keep you hydrated and energized.
• Be prepared for the weather and bring a light jacket or umbrella if needed.
• Be sure to ask questions and interact with the tour guide to get the most out of the experience.
• Be aware of your surroundings and stay safe while biking.

14. Chicago South Side Tour with Optional River Cruise

Source: Chicago South Side

Welcome to the Chicago South Side Tour with Optional River Cruise! This is your chance to explore the vibrant culture and history of one of the most iconic cities in the United States. From the iconic skyline to the bustling neighborhoods, you’ll get to experience the best of what Chicago has to offer. Plus, you can take a relaxing cruise down the Chicago River to get a unique perspective of the city. Don’t miss out on this amazing opportunity to explore the Windy City!

Best time to visit:

Month	Weather
January	Cold, Snowy
February	Cold, Snowy
March	Cool, Chance of Rain
April	Cool, Chance of Rain
May	Warm, Chance of Rain
June	Warm, Chance of Rain
July	Hot, Chance of Rain
August	Hot, Chance of Rain
September	Warm, Chance of Rain
October	Cool, Chance of Rain
November	Cool, Chance of Rain
December	Cold, Chance of Snow

Best time to visit Chicago South Side Tour with Optional River Cruise is during the months of May to September when the weather is warm and there is a chance of rain.

How to reach:

Mode of Transport	How to Reach
Train	Take the Metra Electric Line from downtown Chicago to the Museum Campus/11th Street Station. From there, take the #3 King Drive bus to the South Side.
Bus	Take the #3 King Drive bus from downtown Chicago to the South Side.
Flight	Fly into Chicago O’Hare International Airport (ORD) or Midway International Airport (MDW). From there, take the Metra Electric Line or the #3 King Drive bus to the South Side.

Local tips:

• Take advantage of the free walking tours offered by the Chicago South Side Tour.
• Visit the many museums and attractions located in the area.
• Check out the local restaurants and bars for a unique dining experience.
• Explore the many parks and green spaces in the area.
• Take a stroll along the Chicago Riverwalk for stunning views of the city.
• Take an optional river cruise to get a different perspective of the city.
• Visit the historic Pullman neighborhood for a glimpse into the past.
• Check out the local art galleries and music venues for a unique cultural experience.
• Visit the many shops and boutiques in the area for unique souvenirs.
• Take a day trip to the nearby Indiana Dunes National Lakeshore for a unique outdoor experience.

15. Chicago Haunted Bar Tour

Source: Haunted Bar Tour

Are you looking for a unique and thrilling experience? Then come join us on the Chicago Haunted Bar Tour! Explore the city’s spookiest bars and discover the secrets of their haunted past. From tales of ghostly apparitions to mysterious disappearances, you’ll be sure to have a spine-tingling adventure!

Best time to visit:

Month	Weather	Best Time to Visit
January	Cold, Snowy	Late January
February	Cold, Snowy	Late February
March	Cool, Rainy	Late March
April	Cool, Rainy	Late April
May	Warm, Sunny	Late May
June	Warm, Sunny	Late June
July	Hot, Humid	Late July
August	Hot, Humid	Late August
September	Cool, Rainy	Late September
October	Cool, Rainy	Late October
November	Cold, Snowy	Late November
December	Cold, Snowy	Late December

How to reach:

Mode of Transport	Instructions
Train	Take the Metra Electric Line to the Randolph Street Station. From there, take the #29 State Street bus to the corner of State and Wacker.
Bus	Take the #29 State Street bus to the corner of State and Wacker.
Flight	Fly into Chicago O’Hare International Airport and take the Blue Line train to the Randolph Street Station. From there, take the #29 State Street bus to the corner of State and Wacker.

Local tips:

• Check the tour’s website for the most up-to-date information on the tour’s schedule and cost.
• Wear comfortable shoes and clothing as you will be walking around the city.
• Bring a camera to capture the spooky sights.
• Be prepared to hear some scary stories and tales.
• Be aware of your surroundings and stay with the group.
• Be respectful of the tour guide and other participants.
• Have fun and enjoy the experience!