Chicago
Theme Tours

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Our most recommended Chicago Theme Tours

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

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Chicago River: 45-Minute Family-Friendly Architecture Cruise

2. Chicago River: 45-Minute Family-Friendly Architecture Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a 45-minute cruise sailing down the Chicago River, which features a full-service cash bar and live commentary tailored to entertain the whole family. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago- a perfect way to explore the city free of traffic noise and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

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Chicago: 90-Minute Mob and Crime Bus Tour

3. Chicago: 90-Minute Mob and Crime Bus Tour

Experience Chicago’s underworld of criminals and gangsters on a luxury 90-minute bus tour. Find out how some of the world’s most famous criminals, mobsters, and gangsters conned their way through the city. Ride comfortably in luxury, on a climate-controlled bus, as you see famous Chicago crime scenes that range from the 19th century through modern times. Unlike Chicago walking tours, this Mob and Crime Tour isn’t affected by the Windy City weather. Learn from a local expert tour guide giving interactive live commentary about Al Capone, the Untouchables, the Chicago Mob, John Dillinger, Terrible Tommy O'Connor, H. H. Holmes, the Chicago Black Sox, Leopold and Loeb, bank heists, Cap George Streeter, and more. Grab your camera for a drive-by shooting of the historic criminal courthouse, a Chicago architectural landmark where some of Chicago's most notorious cases were tried. You'll also view historic video footage, receive an informative pamphlet with photos, and can even take part in a crime quiz. Stake out crime scenes like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and other Chicago landmarks. See the site of the St. Valentine's Day Massacre, one of Chicago's most notorious murder scenes. Get off the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. Travel into the criminal past of Chicago's River North, Gold Coast, Lincoln Park, Old Town, Loop, and Magnificent Mile neighborhoods.

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Chicago River: Brunch, Lunch, or Dinner City Cruise

4. Chicago River: Brunch, Lunch, or Dinner City Cruise

Admire the unparalleled riverfront views as you enjoy a fine dining experience on the Chicago River. Arrive early for your 2-hour cruise, dressed to impress. Explore the beautiful Chicago Riverwalk when boarding the boat. The crew will welcome you aboard, and the ship's photographer will record the moment. You'll be escorted to your table in the dining area. With its gorgeous glass-enclosed design, you can enjoy Chicago's incredible architecture from your seat. Savor a delicious meal prepared freshly onboard, and choose to buy a cocktail from the bar.   To add to your enjoyment, the dinner cruise includes music provided by an onboard DJ. During the lunch and brunch cruises, occasional onboard narration will be provided about some of the architectural highlights along the river. On Wednesday and Saturday evenings throughout the summer, you'll have amazing views of the Navy Pier fireworks display. Sample dinner menu Choice of starter: Caesar salad Lobster soup Choice of main course: Jumbo lump crab cakes Maple and mustard glazed chicken breast Braised beef short rib Jumbo forest mushroom ravioli Choice of dessert:  Eli’s original cheesecake Duo seasonal sorbet Chocolate decadent cake Odyssey signature warm butter cake Sample Brunch Menu Choice of starter: Caesar salad Scottish smoked salmon toast Greek yogurt and granola parfait Fresh blueberries and strawberries Choice of main course: Cannellini bean shakshuka Maple and mustard glazed chicken breast Scrambled eggs  Raisin and cinnamon french toast Choice of dessert: Eli's New York style cheesecake Tres con leche flan Triple chocolate mud pie Freshly cut fruit and fresh strawberries Sample Lunch Menu Starter: Caesar Salad Choice of main course: Jumbo forest mushroom ravioli Maple and mustard glazed chicken breast Oven baked Atlantic salmon fillet Braised beef short rib Choice of dessert: Eli's New York style cheesecake Freshly cut fruit and fresh strawberries Duo of Sorbet

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Chicago River Architecture Cruise: Skip-the-Ticket-Office

5. Chicago River Architecture Cruise: Skip-the-Ticket-Office

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 60- or 75-minute cruise of all 3 branches of the Chicago River, and marvel at the architecture that has made the city so legendary. Get an insight into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. Your expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, Marina City, Willis Tower, and more. Relax with a glass of something cold from the cash bar, as you cruise the Windy City’s waterway, and learn its status as a modern metropolis and one of the world’s most beautiful cities. End your tour in the same place where you boarded the boat.

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Chicago Food Tasting: 2.5-Hour Guided Walking Tour

6. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

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Chicago: Gangsters and Ghosts 2-Hour Walking Tour

7. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

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Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

8. Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

Cruise for 2 or 3 hours on Lake Michigan and see the sights of Chicago from a luxury boat, The Odyssey. Board the boat at Navy Pier and enjoy a personal greeting. Smile for the ship's photographer to capture the memory, then embark on an elegant dining cruise along the Chicago shoreline. After being seated at your private table, tuck into your gourmet brunch buffet or 3-course lunch or dinner consisting of creative meals prepared fresh daily by the on-board executive chef. After your meal, dance to the live music or relax on any of the 3 climate-controlled decks as you watch the skyscrapers of Chicago's distinctive skyline glide by. SAMPLE LUNCH AND DINNER MENU Starters (choice of one): Caesar Salad Lobster Bisque (dinner only) Jumbo Shrimp Cocktail (dinner only, available for additional price) Seafood Tower (dinner only, available for additional price) 2.5oz 1/2 Lobster Tail (dinner only, available for additional price) Main Course (choice of one): Jumbo Forest Mushroom Ravioli Oven-Baked Atlantic Salmon Filet Oven Roasted Frenched Chicken Breast with Rosemary and Thyme Braised Beef Short Rib Pan-Seared Fresh Pacific Cod (dinner only) 8 oz USDA Choice Filet Mignon (dinner only, available for additional price) 18 oz USDA Prime Striploin (dinner only, available for additional price) Two 5 oz Broiled Maine Lobster Tails (dinner only, available for additional price) Choice of Dessert:(choice of one): Eli's New York Style Cheesecake Duo of Sorbet Freshly Cut Fruit and Fresh Strawberries Triple Chocolate Mud Pie (dinner only) Odyssey Signature Warm Butter Cake (dinner only) French Macarons (dinner only, available for additional price) Champagne Chocolate Truffles (dinner only, available for additional price) SAMPLE BRUNCH BUFFET MENU Early Risers: Seasonal Fruit Breakfast Pastries Scottish Smoked Salmon Scrambled Eggs Breakfast Meats Breakfast Potatoes Build Your Own Belgian Waffle Station Late Risers: Caesar Salad Shrimp and Farfalle Pasta Salad Potato Salad Roasted Cedar Plank Oregano Salmon Maple & Mustard Glazed Chicken Hand Carved Strip Loin, USDA Choice Desserts: Odyssey Signature Dessert Station Chocolate Fondue Menu items are subject to change.

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Chicago Underground Donut Tour

9. Chicago Underground Donut Tour

Take a donut tour of the windy city, and discover the best Chicago has to offer. At each location, you will taste a curated sample of the best donuts. Some of the stops on this downtown tour include Stan's Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two hour walking tour is led by a passionate donut expert who will guide you to some of Chicago's best donut locales. This tour caters to all size groups, both large and small. The donut tour is great for bachelor and bachelorette parties, birthdays, family reunions, weekend getaways, or even corporate events. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you're excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park & Bucktown neighborhoods to see how "the locals do it". In either case, don't hesitate to join the tour. Buy your tickets today!

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Chicago: 1.5-Hour Lake and River Architecture Cruise

10. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Es un paseo muy bonito, bien explicado, las bebidas a bordo deliciosas, y las fotos que se pueden tomar en el paseo de las 5pm son increíbles, Chicago de noche se ve hermoso.

The tour guide, Jack, was the star of this trip- engaging, knowledgeable, and funny! I would highly recommend a tour with him!

We had beautiful clear skies and really enjoyed the views and listening to the tour guide.

Great tour. Very interesting to learn about Chicago history.

The tour guide for the 2pm sailing was out standing!!