All Chicago Tours &amp; Excursions in 2026 - page 18

Private SUV Transfer from O'Hare Midway Airport to Chicago

1 hourFree Cancellation

from $200

Savor the flavors of Mexico’s Yucatan Peninsula, right in Chicago—and feel like a local when you dine in your host’s own home—during this small-group dinner experience. Be sure to come hungry: alongside a small group of diners, you’ll savor a multi-course menu of Yucatan classics, from a tropical starter to pibil tacos and beyond. In between, enjoy cocktails and the chance to converse with your host and fellow guests.

Yucatan Delights by a Michelin Star-Trained Chef in Chicago

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient pickup and enjoy a scenic drive as your expert guide shares insights about the region. Once at Lake Geneva, you’ll have free time to explore its picturesque lakeside paths, historic estates, and even take an optional cruise. Afterward, immerse yourself in the serene pathways of Anderson Japanese Gardens, where elegant bridges, koi ponds, and peaceful landscapes await. This personalized tour offers a relaxing and enriching experience, perfect for couples, families, and small groups seeking a nature‑filled escape.

(1)

from $205

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

9 to 10 hoursFree Cancellation

3.0

from $1,200

Chicago O’Hare International Airport is a major hub for travel around the world and services more than 30 million people per year, meaning it’s one of the busiest airports. With so many people, the lines for taxis or other modes of transportation can be overwhelming. Prebook this O'Hare Airport ORD to Chicago Arrival Private Transfer Service and ride smoothly from the airport to your hotel.

Special Offer

Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business Car

Arrival Private Transfer: O'Hare Airport ORD to Chicago in Business Car

30 minutesFree Cancellation

Chicago has architecture that stops you in your tracks, a lakefront that stretches to the horizon and neighborhoods full of color and character. With instruction tailored entirely to your group of 2 to 4, you'll quickly get to grips with the skills that separate memorable images from forgettable ones: light, composition, exposure and framing, whether you're on a smartphone or a digital camera. No rushed theory, no generic advice. Just hands-on coaching at your own pace. Then it's out into the city itself. On a guided photo walk through urban landmarks and open lakefront scenes, your instructor will be right there with you, helping you read the light and find the correct frame. Leave with sharper instincts, full control of your device and a collection of images that finally do Chicago justice. Perfect for groups of friends, couples or families, whether you're visiting for the first time or you've lived here for years and never quite managed to capture it the way you imagined.

Private Chicago Photography Class for Stunning City Shots

Private Chicago Photography Class for Stunning City Shots

Experience the freedom of exploring without the extra weighting in Chicago. Our luggage storage service ensures your belongings are secure, allowing you to enjoy the wonders of your destination with peace of mind. Whether you're waiting for a late flight, have arrived early for your stay, or simply want to explore without the burden of your bags, our service is the perfect solution. Store your bags at prime locations near major attractions, transport hubs, and popular areas, making your travel experience smoother and more enjoyable.

from $175

Chicago: Luggage Storage Close to Museum of Contemporary Art

Chicago: Luggage Storage Close to Museum of Contemporary Art

1 dayFree Cancellation

from $10

Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer

Traveling to the airport is too important to leave to chance. Make sure you catch your departing flight on time during this private one-way car transfer between Chicago’s city center and Chicago Midway Airport. Ride comfortably from any hotel or private address in your own chauffeured vehicle. Get dropped off right outside the departures terminal, with pre-booked rides timed to your flight schedule.

Chicago City to Chicago Midway Airport (MDW) - Departure Private Transfer

30 minutesFree Cancellation

from $77

Enjoy a comfortable ride from your hotel or private residence—and get dropped off right outside the departure terminal—during this private one-way transfer from Chicago city center to O'Hare Airport (ORD). Get picked up right outside your door by a professional chauffeur. Travel a well-maintained car, minivan, or minibus, with room for up to 14 people. Free wait time is included in case you’re running late.

Private Transfer from Chicago City to Chicago (ORD) Airport

Private Transfer from Chicago City to Chicago (ORD) Airport

35 minutesFree Cancellation

from $332

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, where cars are absent, allowing horse-drawn carriages to roam freely among Victorian architecture and beautiful scenery. Enjoy iconic sites like Fort Mackinac and Arch Rock while wandering through quaint downtown shops and savoring famous fudge. This tour is designed for families, couples, and solo travelers looking for a serene getaway filled with natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation

Chicago to Mackinac Island Scenic Tour

16 to 17 hoursFree Cancellation

3.0

from $685

Walk through Chicago’s vibrant Jewish history, from the striking Loop Synagogue to the inspiring Heald Square Monument and Jay Pritzker Pavilion. Uncover hidden gems and untold stories that shaped the city’s cultural heart. Book your journey today! Tour is available in following language: English Spanish & French Highlights: • Explore Chicago’s Jewish heritage with a knowledgeable 5-Star Private Guide • Discover key Jewish landmarks and skip common tourist routes with ease • See historic monuments and hidden gems that shaped the city’s vibrant culture • Learn inspiring stories of Jewish contributions to Chicago’s art and history • Get custom tips for more cultural sites and experiences around the city Follow the footprints of Jewish history through Chicago’s vibrant streets!. On this private walking tour with Rosotravel, a Licensed Guide will tailor the experience to your interests, revealing hidden gems, fascinating stories, and historical treasures.

Chicago Jewish History Landmarks Private Guided Walking Tour

Chicago Jewish History Landmarks Private Guided Walking Tour

4.0

from $227

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience

Chicago Exotic Auto Experience

3 to 7 hours

from $1,800

Our transportation service stands out for its reliability, comfort, and private door-to-door experience. Travelers enjoy professional chauffeurs, flight tracking, clean air-conditioned vehicles, luggage assistance, and a smooth direct transfer to Downtown Chicago. Unlike shared transportation, this private service offers personalized pickup, privacy, and a more comfortable travel experience from arrival to drop-off.

ORD Airport to Downtown Chicago Private Transfer

ORD Airport to Downtown Chicago Private Transfer

40 minutesFree Cancellation

from $150

Travel in Comfort & Accessibility with Chicago’s Premier Private WAV Service. Your professional, fully licensed driver will meet you curbside at O’Hare (ORD) or Midway (MDW) and assist with boarding into our wheelchair-accessible Toyota Sienna WAV. ✓ Private, insured service with $350,000+ commercial coverage ✓ Fully wheelchair-accessible vehicles with secure restraints ✓ Safe, quiet ride in a clean, premium vehicle ✓ 16 years of trusted transportation service in Chicago ✓ 5× Certificate of Excellence award-winner on Viator

Wheelchair Accessible Airport Transfer Chicago to O’Hare, Midway

30 minutes to 1 hourFree Cancellation

from $179

Walk beneath Chicago’s soaring skyline, hear its hidden stories, then see it shimmer from the water on a lake cruise. From the iconic Bean to the legendary theatre district, this tour brings the city’s spirit to life—one step and wave at a time. Highlights: • Discover downtown Chicago on foot with a 5-Star Private Guide leading the way • Cruise Lake Michigan with included tickets and audio commentary onboard • See breathtaking skyline views and snap iconic photos from the water • Learn the city’s best-kept secrets through fascinating stories and history • Get tailored recommendations on top spots to eat, visit, and explore next Did you know there’s a sculpture in Chicago that reflects the whole skyline? With Rosotravel’s private tour, you'll walk through the city’s most iconic spots, then see it all again from the water on a relaxing lake cruise. It's a fun, personal way to experience the best of Chicago in just a few hours.Reserve your spot ow!

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

Chicago Downtown Walking Tour & Lake Michigan Cruise Tickets

3 hoursFree Cancellation

4.0

from $263

Step into a welcoming kitchen in Chicago for an immersive Italian cooking class hosted through Cozymeal. Limited to 8 guests, this interactive workshop introduces you to authentic techniques behind pasta-making and classic Italian dishes. The menu you will prepare includes: - Starter: Caesar salad with homemade dressing and Parmesan - Side: Italian garlic bread brushed with olive oil and herbs - Main course: Fresh fettuccine pasta with savory Bolognese sauce - Dessert: Vanilla bean panna cotta with seasonal fruit compote With step-by-step guidance from your local pasta chef, you’ll enjoy a hands-on approach to mastering Italian cooking. Guests are welcome to bring wine or beer to complement the meal and celebrate the flavors of Italy.

Artisan Italian Pasta Class in Chicago (Includes 4-Course Meal)

Artisan Italian Pasta Class in Chicago (Includes 4-Course Meal)

Unleash your creativity at a private Art Splash painting session in Chicago. Perfect for group celebrations, birthdays, or corporate events, this 40-minute experience lets you get hands-on with bold paints, premium tools, and a 12x16 canvas to take home. Protective clothing is provided—so you can embrace the splash, layer colors, and express yourself freestyle, no art skills needed! Your group gets a private room and expert guidance, ensuring an unforgettable, laughter-filled activity for anywhere from 6 to 80 people. Just arrive ready for creative fun and leave with a unique piece of art (allow up to five days for full drying).

from $162

Private Art Splash: Chicago Group Painting Experience

Private Art Splash: Chicago Group Painting Experience

40 minutes

This 45-minute self-guided walking tour explores the bizarre history beneath Wicker Park’s elegant surface. Led by a longtime resident, you will discover the neighborhood’s transition from a wealthy enclave to a gritty artist hub and its modern gentrification. Key Highlights: * Radical History: Learn about labor leader Lucy Parsons and the search for hidden bombs in the park. * Beer Baron Row: Hear tragic tales of murder and madness tied to grand Victorian mansions. * Quack Medicine: Discover how Theophilus Noel’s "Vita-Ore" empire funded iconic local architecture. * Mob Intrigue: Visit the former Russian Baths where mobsters met in steam rooms to avoid FBI wires. * Massacre Connections: See where the St. Valentine’s Day Massacre was planned and its getaway car destroyed.

from $70

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

Bizarre Wicker Park: Medicine and Mobsters Self-Guided Audio Tour

45 minutes to 1 hour 15 minutesFree Cancellation

3.0

from $10

Chicago Photography Masterclass Private Photography Lesson

This tour is special because it combines a personalized street and night tour experience with expert photography guidance in Chicago. You’ll explore both iconic landmarks and hidden streets, capturing the city’s character from golden hour through to its dazzling night lights. As skyscrapers glow and trains blur past, your professional guide helps you master techniques like composition, long exposure, and low-light shooting. Designed around your skill level, this private tour ensures one-on-one coaching, creative development, and unique photo opportunities. It’s more than sightseeing—it’s a hands-on journey through Chicago’s streets after dark, where every corner becomes a chance to create striking images. Creative composition, using lines, repetition, camera angles Training your eye: finding subjects, lighting, composition Taking control of your camera: f-stop, shutter speed, ISO and focusing Reviewing your photography

Chicago Photography Masterclass Private Photography Lesson

3 hoursFree Cancellation

from $140

Get to grips with Italian pasta in this Florentine-inspired hands-on class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs. Carpaccio, hand-filled ravioli, a fresh vodka sauce and citrus cookies – four courses, four distinct techniques, one deeply satisfying Italian meal. Your hands-on cooking experience features: - Marinated Vegetable Carpaccio – assorted vegetables, homemade herb dressing and fresh herbs - Beef Ravioli – flour, eggs and seasoned beef - Vodka Sauce – olive oil, tomatoes and vodka - Italian Lemon Drop Cookies – flour, butter and eggs You will leave with real pasta-making skills and a fresh perspective on Italian cuisine, from antipasto to dessert. Guests are welcome to bring wine or beer to enjoy throughout the experience.

Italian Ravioli Cooking Class in Chicago (Includes 4-Course Meal)

Italian Ravioli Cooking Class in Chicago (Includes 4-Course Meal)

2 hours 30 minutesFree Cancellation

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour small group (12 Guest Maximum) guided walking tour is perfect for busy sidewalks and getting up close to monumental art! Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

from $145

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

2 hours 30 minutesFree Cancellation

(5)

from $55

Little Diners Crew invites young food enthusiasts aged 4-12 to embark on culinary adventures that expand their palates beyond mac-n-cheese and chicken fingers. Each month, kids explore different cuisines at Chicago's best restaurants while interacting with chefs, tasting and rating new dishes, and learning about food preparation and dining etiquette. Meals become memorable experiences as kids discover the world through food.

Little Diners Crew Culinary Adventures for Kids

Little Diners Crew Culinary Adventures for Kids

from $105

Fresh, vibrant and built on ingredients you can find anywhere – this Mediterranean cooking class in Chicago, hosted through Cozymeal, which connects you with top-rated local chefs, teaches three crowd-pleasing dishes that bring the coast straight to your kitchen. Your hands-on cooking experience features: - Hummus with chickpeas, lemon, cumin and olive oil - Greek Chicken With Lemon and Feta with chicken breast, Feta, thyme, lemon and white wine - Balsamic Berries With Greek Yogurt with Greek yogurt, honey, balsamic vinegar and mixed berries You will leave ready to recreate a full Mediterranean spread at home – from hummus to dessert. Guests are welcome to bring wine or beer to enjoy throughout the experience.

Mediterranean Cooking Class in Chicago (Includes 3-Course Meal)

Mediterranean Cooking Class in Chicago (Includes 3-Course Meal)

2 hours 30 minutesFree Cancellation

Custom Chicago Walking Tours

from $110

1 to 3 hoursFree Cancellation

(4)

from $75

Winner of 10 Best History Tours by USA Today in 2026, and the "ORIGINAL" Chinatown tour since 2001. Discover the history, culture, and hidden stories of Chicago’s Chinatown on a guided walking tour through one of the city’s most vibrant neighborhoods. Starting at Chinatown Library, you'll visit iconic landmarks, including Chinatown Square, Chinatown Mural, Ping Tom Memorial Park, the Chinatown Gate, Nine Dragon Wall, Pui Tak Center, Chinese Buddhist Temple, St. Therese Chinese Catholic Church, and more. Along the way, you'll learn about Chinese heritage, local traditions, and the community’s lasting impact on Chicago before ending at the historical old Chinatown. - Explore Chicago Chinatown with a knowledgeable guide. - Learn about Chinese culture, history, and traditions. - Admire public art and the Chinatown Mural - Perfect for first-time visitors and returning guests alike

Chinatown History and Culture Tour

1 hour 30 minutesFree Cancellation

Chicago Sightseeing River and Lake Cruise

from $25

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Travis_M, Aug 2026

Enjoyed

Just had a little problem finding a place to park but called the vendor and the young lady that answered the phone was very patient and helpful. Very good tour. Our narrator Jupiter, did a good job of pointing out all the sites and answering questions.

Chicago River 90-Minute Architecture Tour

Cheyenne_S, Aug 2026

Tour guide was really...

Tour guide was really fun, had lots of insight about the history and architecture of the city. This specific trip took us all the way north to goose island, south to chinatown, and out to the pier. Drinks on board the ship were good but in small cups, the funds went to a non-profit so we didn't feel that bad about it. I highly recommend going around sunset if you can, it's the best time. We wound up being late to our reservation and the staff was kind enough to reschedule us for the next hour.

Flyover in Chicago

Charnique_W, Aug 2026

10/10 highly recommended

My daughter and I loved this experience. Purchasing our ticket on Viator was so much easier, I absolutely loved how it showed up on my phone screen as a reminder of the event for the day when added to my wallet. The place was clean and the staff was nice. We went on a weekday so the line was short and we got in, in less than 5 mins. I would definitely do this again!!!!

Chicago Architecture River Cruise

Breah_C, Aug 2026

This was so enjoyable! We...

This was so enjoyable! We did the 8:30pm tour, which I would highly recommend. The entire city is lit up making for the most breathtaking views. Sam S was our guide (the best guide for sure) and his knowledge along with charismatic presentation truly made the entire experience top notch. With the availability of the bar and snacks on deck, I could have stayed on board for hours. The information given during the tour were things I truly had never heard before and kept my attention the entire time. It was a very smooth ride and the boat seemed to make no noise at all allowing for no issues hearing Sam S or the quiet sounds of the city around. 100/10 experience!

Chicago Architecture Center River Cruise aboard First Lady

Judith_L, Aug 2026

Architecture tour worth doing again

Michael the mapmaker was a fantastic docent for the tour, and we had a perfect summer day for this tour. He was full of historical tidbits and knowledge about the skyscrapers throughout downtown Chicago. I’ve been on this tour before, and Michael and the weather made it well worth repeating.

Chicago By Night River and Lake Cruise

Deidre_S, Aug 2026

A great experience

First Lady boat ride was a great experience. You will start on the Chicago river and merge into the Michigan lake. The view was amazing I mean amazing especially at night! The con was it can get a little bit chilly at night so bring a jacket. They sell blankets if you were to get cold and they also have a bar so you can sip and enjoy the ride. I would definitely recommend it.

Chicago Lake and River Architecture Tour

Liliana_B, Aug 2026

Could not recommend Emma enough!!

Emma our tour guide to the fantastic job! It was such a fun and engaging tour and we got to see so much of Chicago in the hour and a half. The AC worked well and you were able to get drinks while I’m bored and of course, go in and out as you please. The bathrooms were clean and the stuff was all very helpful and knowledgeable. Highly recommend!

Chicago Favorites Ultimate Food and Walking Tour

DavidFran_B, Aug 2026

A Delicious Tour Filled with History, Great Food & Generous Portions!

Brayden was an amazing tour guide. He provided lots of relevant information and interesting facts that brought Chicago's history to life. The food tour exceeded my expectations. I've been on many food tours where the portions were quite small, but this tour was completely different. Every stop provided generous portions, along with a bit of history and background about the food and area. You definitely won't leave hungry! You'll leave with a full belly and a much better understanding of Chicago's history and culture. A must do if you're ever in Chicago. I highly recommend this tour.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Autumn_V, Aug 2026

Kay Made This One of the Highlights of Our Chicago Trip!

We absolutely LOVED this tour! We packed a lot into our time in Chicago, but the river architecture tour was easily one of the highlights of the entire trip. The views from the river are incredible, and seeing Chicago’s architecture from that perspective gives you a completely different appreciation for the city. But what really made the experience exceptional was our tour guide, Kay. She was phenomenal! She was incredibly knowledgeable without ever making the tour feel like a lecture, and she had the perfect combination of history, architecture, storytelling, humor, and personality. You could tell she genuinely loves Chicago and knows her stuff. Kay kept us engaged the entire time and pointed out so many details we never would have noticed on our own. We learned a ton, laughed a lot, and found ourselves looking at the city completely differently by the end of the tour. Even if you aren’t someone who thinks you’re particularly interested in architecture, DO THIS TOUR. The river itself is beautiful, the skyline is spectacular, and with a guide like Kay, the experience is so much more than just sightseeing. If you have the opportunity to request Kay, absolutely do it. She made an already fantastic Chicago experience unforgettable. We would recommend this tour and Kay specifically without hesitation!

Lake Michigan Skyline Cruise in Chicago

Stanley_A, Jul 2026

We had a great experience...

We had a great experience on the Skyline Cruise in Chicago. The staff was extremely friendly and welcoming from start to finish. The boat ride was smooth, and the views of the city were absolutely beautiful. We also enjoyed learning about Chicago’s landmarks and history throughout the tour. I would highly recommend this cruise to anyone visiting Chicago—it’s a relaxing, scenic, and educational experience!