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Best of Chicago Tour





The Best of Chicago Tour is curated for curious travelers who want to discover the charm and spirit of Chicago. In just four hours, this small-group city tour takes you through the famous landmarks of the city including Buckingham Fountain, Cloud Gate (Chicago Bean) and Adler Planetarium Pier. You'll also enjoy the Shoreline Architecture Cruise along the Chicago River from where you will see over 40 iconic buildings. With hotel pickup and drop-off included, skip-the-line access, and a maximum of six guests, it’s one of the best Chicago city tours for anyone short on time but big on discovery.
What you'll see

Starbucks Reserve Roastery Chicago
Starbucks Reserve Roastery Chicago turns coffee into an immersive experience with rare brews, live r...

Chicago Pedway
Uncover the Chicago Pedway an underground walkway linking transit, shops, and landmarks, offering a ...

Cloud Gate (Chicago Bean)
The first public outdoor installation of British artist, Anish Kapoor. Cloud Gate or the Chicago Bea...

Shoreline Architecture Cruise
Narrated boat tour through the Chicago River where you will learn about the the history behind the c...

Buckingham Fountain Chicago
Immerse yourself in the beauty of Buckingham Fountain, a Chicago landmark known for its captivating ...

Millennium Park
Discover Millennium Park. Chicago’s cultural hub with iconic art, live music, gardens, and year-roun...

Navy Pier
Experience Navy Pier, Chicago’s lakefront playground rides, cruises, gardens, dining, and skyline vi...

Chicago Riverwalk
Discover the Chicago Riverwalk is a scenic 1.25-mile urban oasis with dining, art, history, and skyl...

Crown Fountain
Experience Crown Fountain in Millennium Park where digital faces, cascading water, and playful inter...
Highlights
- Relax on Shoreline Architecture Cruise and see over 40 iconic Chicago landmarks from the river
- Capture stunning views of Chicago’s skyline and Lake Michigan from Adler Planetarium Pier viewpoint
- Visit to Cloud Gate (The Chicago Bean) – One of the city's most iconic public art pieces
- Make a brief stop at Buckingham Fountain – One of the largest fountains in the world
Includes
Excludes
Description
Experience Chicago through a thoughtfully designed The Best of Chicago Tour. It's a small-group tour on which you explore the city’s architectural beauty, cultural icons, and lakeside charm in just four hours. This tour is limited to just six guests to make it a more relaxed pace and meaningful to explore one of America’s most architecturally celebrated cities. Each stop adds depth to your understanding of Chicago’s character, blending history with modern-day marvels.
Your tour begins with your local guide picking you up from your downtown Chicago hotel in a luxury van. Then you make the first stop at Adler Planetarium Pier to see one of the most impressive views of the Chicago skyline. With Lake Michigan stretching beside you and the city’s silhouette rising in the distance, you will have plenty of opportunities to take postcard-worthy images.
After Adler Planetarium Pier, you will board the Shoreline Architecture Cruise to take a narrated boat ride along the Chicago River. If Chicago’s architecture and urban development fascinate you, this experience will stand out as you will cruise past more than 40 significant structures including the neo-Gothic Tribune Tower and the glassy curves of Aqua Tower making it one of the most fun tours in Chicago. Meanwhile your local guide will narrate historical context and stories behind the buildings, making this more than just a sightseeing ride.
Next, you'll stop at Buckingham Fountain. The fountain is constructed of Georgia pink marble and has 193 jets that push out 14,000 gallons of water per minute during a display.The design of this fountain was inspired by the Latona Fountain at the Palace of Versailles, but its presence in Grant Park feels uniquely Chicagoan. The fountain nestles in a green space from where you can have city views which make the atmosphere feel serene making it a perfect place to pause and relax.
The tour wraps up at Cloud Gate, better known as “The Bean.” This huge, bean-shaped, reflective sculpture was sculpted by British-Indian artist Anish Kapoor in 2004. It has become one of the most recognizable public art pieces in the country. While you marvel at this art piece, your guide will share the artist’s intent and his inspiration.
After visiting these sites, your guide will return you to your downtown Chicago hotel, leaving you with a deeper appreciation for the city’s balance of beauty, innovation, and thoughtful design.
Important Information
Know Before You Book:
- The exact length time for a tour may vary slightly based on traffic and seasonality (during off-peak times, tours tend to be a little shorter due to less traffic.
- The cruise is replaced with a Field Museum during winter.
- The lead traveler’s name is needed for all bookings.
- Full names of all travelers are required when making a reservation.
Know Before You Go:
- Don’t forget to bring a camera to capture the highlights and some spending money for souvenirs along the way.
- This tour involves a moderate amount of walking so it’s advisable to wear comfortable walking shoes.
- Check the weather forecast and dress appropriately for the conditions
- Pick up time will be confirmed 1-3 days prior to the tour date via email or phone. If you do not have access to these, please be ready 30 minutes before the tour start time in the hotel lobby.
Not Recommended For:
- Individuals with mobility challenges
- Individuals with heart conditions
Our Guest Reviews

4.5/5
I took my family of 5 on this exceptional tour and we had the BEST EXPERIENCE. I was very impressed with the knowledge and history of Chicago as well as all the experiences packed into the tour. Definitely was the best part of our family trip to Chicago!

5/5
This trip was a lot of fun, definitely recommend it! It was just two adults in my group. But then, we were also in a group with one mom and two daughters and everybody seemed to have a blast!! The drive was very nice as well. Plus it's great that they pick you up at your hotel. I'm definitely not brave enough to drive in Chicago!!

5/5
MUST DO. This was the best tour of our 5 day trip. All thanks for Mohammed! He was amazing: friendly, fun, and welcoming. He helped over come some fears (in our group) and we all are thankful for an unforgettable trip. made us feel right at home and was full of conversation about the city and places we visited. A++++
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