Things to do in Chicago, Illinois (IL): The Best Self-Guided Tours & Rentals

September 1, 2021 Darwin Bolte

The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago

1. Chicago Full Day Bike Rental

540 N Lake Shore Dr, Chicago, IL 60611, USA Bobby's Bike Hike Chicago
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4.9 based on 37 reviews

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

Inclusions: Use of bicycle and helmet, Detailed city map, Bike lock

Exclusions: Guide, Food and drinks

Reviewed By rhondae476

Gabe is an amazing tour guide. He provided great information on the history of Chicago and the food we were sampling. I love that they support local independent businesses.

2. Chicago Scavenger Hunt: Chicago's Magnificent Mile

399 N Michigan Ave, Chicago, IL 60601, USA Let's Roam Chicago
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Named for the cable car turnarounds and the prominent elevated railway that encircled the area at the end of the 19th century, the Loop is Chicago's commercial and cultural core. On today's epic scavenger hunt of Chicago, you'll uncover the area's best sights and rich history. Along the way, you'll visit Cloud Gate, Art Institute of Chicago, and the Federal Reserve Bank of Chicago. It's time to strap on those walking shoes, round up some friends and book your Chicago Loop scavenger hunt today! What You'll See: Tiffany Dome, The Bean, Crown Fountain, Art Institute of Chicago

Inclusions: All taxes, fees and handling charges, Local taxes

Exclusions: Transportation to/from attractions, Food and drinks

3. Chicago Scavenger Hunt Adventure

320 N Dearborn St, Chicago, IL 60654, USA Urban Adventure Quest

Turn Chicago into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walking tour. Guided from any smart phone, teams make their way among well known and overlooked gems of the city, solving clues and completing challenges while learning local history.

Inclusions: One Scavenger Hunt Tour for a team of 2-5 people.

Exclusions: Smart phone

Reviewed By bpguy10

What a fun way to see Memphis and learn about Memphis. We’ve been to Memphis before but learned a lot and a fun doing it.

4. Explore Chicago with a Unique Scavenger Hunt by Operation City Quest

36 W Wacker Dr, Chicago, IL 60601, USA Operation City Quest Scavenger Hunt of Chicago

Operation City Quest of Chicago is a great way to see the city in a fun way! You'll use an app on your phone to submit photos of items you find around the city. For every photo you submit, you'll get points. You'll be able to see your score on the rankings after compared to all who have played across the country. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Chicago.

Inclusions: All Activities, 2 hours with a remote interactive guide, GST (Goods and Services Tax)

Exclusions: Use of Activity-owned smartphone, Private transportation

5. Chicago Lakefront Electric Bike Tour

447 S Columbus Dr, Chicago, IL 60612, USA Chicago E-Bikes

This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will get a chance to ride Electric Bikes and see the city from a different vantage point. It all begins navigating through Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus). As we admire the grounds and perfect location between the iconic skyscrapers and nature. We will then proceed and make our way over to the lakefront path. Riding along we will take you to a magnificent view of the skyline which is the best place for a photo shoot. Afterward, we will take the lakefront bike path over the Chicago River and past Navy Pier. A quick ride back to our starting point ends the tour.

Inclusions: Use of bicycle, Helmets, Bottled water, Snacks

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6. The Chi-Town Showdown Scavenger Hunt

Cloud Gate, 201 E Randolph St, Chicago, IL 60602, USA Alley Kat Adventures

Alley Kat Adventures is an Austin, TX-based event design company offering city scavenger hunts in 30 cities in the US and Mexico as well as custom events worldwide. Our specially hand-crafted, interactive quests are equal parts tour, cultural experience, creative challenge, detective hunt, & social experiment! Guests get to discover hidden gems off the beaten trail while completing fun missions! Find an obscure repeating theme in various street art around town, marvel at giant digital art curated just for you, hunt down an iconic and locally famous old elevator, and more!

Inclusions: scavenger hunt document

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Reviewed By Dianne F

Great way to learn about Fort Lauderdale. I live here but had a friend visiting and it was fun for both of us. This would be great for a group of friends, coworkers, or bachelorette party. The remote adventure coach, Katie, was great- helpful when needed!!

7. Chicago Ghost Hunt: Ghosts of the Chicago River

24 W Randolph St, Chicago, IL 60601, USA Let's Roam Chicago

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Inclusions: All taxes, fees and handling charges, Digital Copies of your scavenger hunt photos, Local taxes

Exclusions: Food and drinks, Transportation to/from attractions

Reviewed By 311kimberlys

There was no explanation of how to begin my tour through the app. I was never able to get it to work so I didn't do the tour.

8. Chicago Scavenger Hunt: A Day At The Zoo

2001 N Clark St, Chicago, IL 60614, USA Let's Roam Chicago

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Inclusions: All taxes, fees and handling charges, Digital Copies of your scavenger hunt photos, Local taxes

Exclusions: Food and drinks, Transportation to/from attractions

Reviewed By 311kimberlys

There was no explanation of how to begin my tour through the app. I was never able to get it to work so I didn't do the tour.

9. Unique Scavenger Hunt Experience in Chicago by Wacky Walks

36 W Wacker Dr, Chicago, IL 60601, USA Wacky Walks of Chicago

Walk around Chicago while completing the Wacky Walks scavenger hunt. Use an app to find a list of objects around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others around the country! All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Chicago.

Inclusions: 2 hours with a remote interactive guide, All Activities, GST (Goods and Services Tax)

Exclusions: Use of Activity-owned smartphone, Private transportation

10. Adventurous Scavenger Hunt in Chicago by Crazy Dash

36 W Wacker Dr, Chicago, IL 60601, USA Crazy Dash of Chicago

You'll use an app to explore Chicago in this fun scavenger hunt. Use the app to find things around the city, take photos and collect points. At the end, take a look at the rankings to see your score compared to other teams across the country. All our Scavenger hunts have a live remote host to help along the way. Come out and explore with us in Chicago.

Inclusions: 2 hours with a remote interactive guide, All Activities, GST (Goods and Services Tax)

Exclusions: Use of Activity-owned smartphone, Private transportation

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