Chicago Sightseeing Tours
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Chicago Sightseeing Tours: 9 Ways to Experience the Best of the Windy City

When it’s your first time in Chicago, you want to experience it all—from the culinary scene to the iconic landmarks. But with so much to see in such a short amount of time, you’ll drive yourself crazy trying to mastermind the perfect itinerary. Instead, take advantage of the Chicago sightseeing tours throughout the city for the ultimate experience. Best of all, no matter which sightseeing tour you choose, you’ll discover the best of Chicago.

My recommendations for the best Chicago sightseeing tours include:

Tourists wait to board the Chicago Double Decker tour bus
Chicago Trolley & Double Decker Bus Tours

1. Chicago Trolley & Double Decker Tours

It’s hard not to notice the Red and Green trolleys and Big Red Double Decker buses as you explore Chicago. Why not hop on and see the sights? This hop-on, hop-off style tour covers 13 miles of Chicago’s prominent downtown area and landmarks. Choose from a 1, 2, or 3-day ticket and see as much of Chicago as possible.

The beauty of the Chicago Trolley & Double Decker tour is the ability to hop on and hop off wherever and as often as you please. You can create your own Chicago sightseeing tour while taking advantage of the convenient transportation.

Passengers listen to a tour guide on Seadog Chicago Cruises on the Chicago River
Seadog Chicago Cruises

2. Seadog Cruises Chicago

Departing from Navy Pier, Seadog Chicago Tours provides epic views of landmarks such as Grant Park, the Chicago Harbor, Buckingham Fountain, and more. This seasonal cruise operates from March through October annually.

Choose between a thrilling speedboat tour of the lakefront or a leisurely 75-minute architectural tour of Chicago’s buildings and landmarks. These Chicago sightseeing tours are quite popular thanks to their location and nature, so reserve your seat ASAP.

Woman bites into a chocolate bar in a city
Satisfy your sweet tooth on a Chicago Candy Tour.

3. Chicago Candy Tours

Do you have a sweet tooth? I sure do!

Chicago Candy Tours pair tourists with renowned pastry chef, Jenny Lewis, for a walking tour through Chicago’s candy history. Along the way, you’ll learn about Chicago’s place in the candy industry and some sweet facts about the delectable treats, too. And, of course, what candy tour would be complete without a sampling! At the end of your tour, you’ll bite down on sugary treats made right in Chicago.

For those who prefer chocolate to hard candy or fruity sweets, book a spot on the Chocolate Tasting Tour, Food of the Gods, Chicago Style tour.

Crowd of tourists gathers outside a Chicago building to listen to a tour guide
Chicago Crime Tours

4. Chicago Crime Tours

Perhaps you prefer your Chicago sightseeing tours to have a bit of an edge to them. Fans of crime shows and Chicago’s harrowing history will love what they learn on a Chicago crime tour.

You’ll walk in the footsteps of notorious criminals such as Al Capone and see the locations of infamous crime scenes. The 90-minute tour requires a bit of walking but includes transportation on a luxury mini-bus as well.

Due to the nature of the tour, it is recommended that children ages 6 and under to not participate.

Tourists clink beer glasses together on a bar tour
Historic Chicago Walking Bar Tour

5. Historic Chicago Walking Bar Tour

If your definition of sightseeing includes visiting Chicago’s historic bars, this is the tour for you. The Historic Chicago Walking Bar Tour visits some of the Windy City’s most notable bars, pubs, and speakeasies. Your local guide will tell you all about each bar’s history along with information about how the Prohibition affected the city.

While not too much walking is included, the tour includes three drink stops where you’ll taste and sample local brews, wines, and cuisine. This tour is the perfect combination of sightseeing, history, and delicious Chicago food.

Bus outside of Chicago Harbor
See It All Tours / Facebook

6. Chicago Mini Bus Tour

Operated by See It All Chicago Tours, the Chicago Mini Bus Tour includes three photo stops, unparalleled sights, and a comfortable bus ride. Of the Chicago sightseeing tours available, this choice is ideal for those who’d like to see it all without a tremendous amount of walking.

The bus tours include sights from Soldier Field to Michigan Avenue and everything in between. Tours operate from March to December, Tuesdays through Sundays.

Helicopter flies over Chicago at dusk
Chicago Helicopter Experience

7. Chicago Helicopter Experience

Truth be told, a lot of Chicago sightseeing tours and landmarks are crowded with tourists. To escape the crowds and amplify your Chicago vacation, take a helicopter tour! Not only will you get the best view of all Chicago landmarks, you’ll also experience the rush of a lifetime. Sure, you can go to observation decks at the top of skyscrapers for epic sightseeing, but a helicopter can take you even higher!

Operated by Chicago Helicopter Experience, riders can choose between a daytime or nighttime tour. Each tour provides jaw-dropping cityscapes, endless photo opportunities, and information about Chicago.

Bobby’s Bike Hike / Facebook

8. Bikes, Bites & Brews Tour

This tour is ideal for those interested in devouring Chicago’s legendary food groups—pizza, hot dogs, cupcakes, and beer. The Bikes, Bites & Brews Tour winds through Chicago neighborhoods including Lincoln Park, Streeterville, the Gold Coast, Lakeview, and Wrigleyville for samples of the area’s best bites. And, you won’t have to worry about an excess calorie intake. You’ll bike it all off along the way.

You don’t need to be a pro cyclist to participate in this tour either. So long as you know how to ride a bike, you’ll be just fine. Throughout the tour, you’ll learn more about Chicago’s various neighborhoods from your local tour guide.

Chicago's Lincoln Park
See all the city has to offer on the Chicago Grand Half-Day Tour.

9. Chicago Grand Half-Day Tour

The Chicago Grand Half-Day Tour is the ultimate sightseeing experience. First-time visitors who want to learn all about Chicago and see the iconic landmarks should book this tour right away. The tour encompasses the North and South side of Chicago along with several photo opportunities.

This 4-hour tour is ideal for visitors who see the sights and still have a good portion of their day left to explore. And, with multiple departure times, guests can choose the tour time that fits their travel schedule or preferences.

5 Tips for Enjoying Chicago Sightseeing Tours

No matter which of the recommended Chicago sightseeing tours you choose, I want you to have an awesome time! Keep these tips in mind as you book and depart on your chosen tour of Chicago.

Book in Advance

As you can imagine, Chicago sightseeing tours are a popular activity choice among tourists. In peak vacation season, these tours fill up fast. To ensure you reserve a spot on the tour you want, book as far in advance as possible.

In addition to guaranteeing a spot on the tour, you may be able to take advantage of certain discounts or deals to lower the price of your tour.

Follow the Instructions on Your e-Ticket or Voucher

Once you’ve booked your tour, you will receive either an e-Ticket, voucher, or email with further instructions. These instructions can include:

  • Directions to confirm your tour time and spot
  • Where to meet for the tour.
  • Tour details and rules

It is imperative that you follow these instructions exactly as written. If you fail to do so, you may forfeit your tour time or end up at the wrong departure location.

Dress Appropriately

Chicago’s weather ranges from scorching hot summers to blistering cold winters. Look at the weather forecast for your trip and dress appropriately. This packing list will help you determine what to pack and wear for your tour.

For the best tour experience, wear weather appropriate attire, comfortable walking shoes, sunglasses, and a light jacket.

Pack the Essentials

You’ll also want to bring a few items along for a pleasant tour experience. Bring a backpack or day bag with the following things:

  • Valid Photo ID
  • Wallet with Extra Cash
  • Phone Charger
  • Phone or Camera for Photo Opportunities
  • Sunblock (during the summer)

Be a Good Tourist

While on your tour, be sure to follow any and all rules provided by your guide. These rules are in place for your safety and to ensure you have a fantastic tour experience.

In addition, be respectful of others in your tour group. Don’t cut in front of them for a photo opportunity or talk loudly over the tour guide.

Chicago Sightseeing Tours: Book Yours Today

Remember! Tours in Chicago fill up fast, so reserve your spot as soon as possible.

Which of our recommended Chicago sightseeing tours are you most interested in?

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