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ChicagoOutdoor activities

Our most recommended Chicago Outdoor activities

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.

Chicago: 1.5-Hour Lake and River Architecture Cruise

2. 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.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

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

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. 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, exploring 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.

Chicago: Big Bus Hop-on Hop-off Open-Top Sightseeing Tour

4. Chicago: Big Bus Hop-on Hop-off Open-Top Sightseeing Tour

Experience the Windy City with our hop-on, hop-off double-decker sightseeing bus tour, or a panoramic sunset tour. Marvel at the stunning skyscrapers of Chicago, including the iconic John Hancock Center, the towering Willis Tower, and the historic Wrigley Building. Our engaging and professional digital commentary will provide you with fascinating facts and insights into Chicago's rich history as you explore the city's most impressive landmarks. Hop on and off as many times as you want to visit attractions such as the world-renowned Shedd Aquarium and Field Museum of Natural History. Marvel at stunning Lake Michigan, see the skyline from 360 CHICAGO, or take a stroll on the renovated Chicago Riverwalk. When you're ready, Big Bus will be back to pick you up. Download our free app for real-time bus tracking. Travel along the famous Magnificent Mile, considered one of the world's great avenues, to shop 'til you drop at the many flagship stores along the boulevard. Then cross over the Michigan Avenue Bridge, which offers breathtaking views of the Chicago River. With our convenient stops located throughout the city, it's easy to cruise through The Windy City without needing to navigate traffic or public transportation. Choose between a 24 or 48-hour ticket, and take your time discovering all that Chicago has to offer.

Chicago: 1.5-Hour Romantic Sunset Cruise

5. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire 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. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. 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.

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

6. 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.

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 your historian guide revealing the many interesting stories hidden behind each turn. Explore the Chicago Loop, known as the vice district during the 1920s and 30s, once the home of speakeasies, secret tunnels and bootleggers. 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 including Chicago Riverwalk, Death Alley, and the Chicago Theatre. Peak inside the haunted Palmer House. Finish up at the Congress Hotel, one of the most haunted places in Illinois. Enjoy frequent stops along the way, including a refreshment stop and a restroom break.

Chicago: Go City Explorer Pass Choice of 2-7 Attractions

8. Chicago: Go City Explorer Pass Choice of 2-7 Attractions

With the Chicago Explorer Pass by Go City you can visit top sites such as the Navy Pier, Skydeck Chicago, or The Field Museum, all on one handy pass. Enjoy great savings on admission to your choice of 2 to 7 top Chicago attractions and tours, and pay nothing at the gate. Explore at your own pace on a hop-on and hop-off Chicago bus tour, or aboard one of two lake cruises. You have 60 days to use your pass from your first attraction visit. To help you create your own itinerary you'll also get a free digital guide. Use it to help you decide what to do, where to go, and how to get there. The most popular activities require advanced reservations, check instructions on the included Go City guide, and make sure to place reservations well in advance to avoid disappointment. Included Chicago attractions to choose from with your Explorer Pass: • Hop-On Hop-Off Big Bus Chicago: 1-Day Classic Tour • 360 CHICAGO (reservations required) • Skydeck Chicago (reservations required) • Navy Pier Ferris Wheel and Rides • Adler Planetarium • 10pin Chicago 90-minute Bowling & Pizza (reservations required) • America Writers Museum • Shoreline Architecture River Cruise • Field Museum • Museum of Science and Industry • LEGOLAND Discovery Center • Bike Chicago: 2 Hour Bike Rental • Chicago Children's Museum • Frank Lloyd Wright Home and Studio Tour • Chicago History Museum • Museum of Contemporary Art • Robie House • Chicago Theatre Marquee Tour • Downtown Chicago TV & Movie Sites Walking Tour • Ernest Hemingway Birthplace Home • The Forge Adventure Park • Lincoln Park Zoo Rides • $20 Food and Drinks Credit at The Cauldron Chicago • Chicago Must-See Architecture Walking Tour • Mobsters and Haunted Mysteries Walking Tour • Chicago Pizza and Drink Combo *Savings based on itineraries on Go City website.

Chicago: Lake Michigan Skyline Tour & Lake Hopper Cruise

9. Chicago: Lake Michigan Skyline Tour & Lake Hopper Cruise

Immerse yourself in the sights and learn about Chicago’s history and architecture during a cruise on Lake Michigan. Take advantage of skip-the-line entry privileges with a barcoded ticket that lets you proceed directly to the boarding line. Whether you’re a local or a visitor to the city for the first time, taking in the spectacular views of Chicago's skyline from the lake makes for a perfect outing. You’ll see the city as never before while listening to commentary on Chicago's history and architectural gems. Simply hop on board, sit back, relax, and enjoy as you admire Chicago's most significant landmarks and striking buildings that make up the city's skyline that has appeared in so many movies and TV shows. Route: The Skyline Tour and Lake Hopper takes you out onto Lake Michigan, heading both north and south on the lake, you’ll see many of Chicago’s famous landmarks and the classic skyline vista. Enjoy the flexibility to hop-on and hop-off the Skyline Lake loop at either the Museum Campus or Navy Pier.

Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

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

Discover Chicago's sparkling skyline from Lake Michigan on a sightseeing cruise. Savor a mouthwatering meal while listening to music played by a live DJ. Sip on unlimited coffee and tea while gazing out at sights like Navy Pier, Grant Park, and Willis Tower. 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 meal. Enjoy a creative meal prepared fresh by the onboard chef. Following your meal, dance to live music or relax on any of the 3 decks as you watch the skyscrapers of Chicago's distinctive skyline glide by.  Sample Brunch Menu:Early Riser:Breakfast Pastries Scrambled EggsBreakfast Meats Breakfast Potatoes French Toast Late Risers:Kale Quinoa SaladGreen Goddess Pasta SaladCaesar Salad Oven Roasted WhitefishKid's Station Hand Carved Strip Loin Hand Carved Oven-Roasted Turkey Dessert: Cakes, Brownies, Seasons Fruit 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) 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) Menu items are subject to change.

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Frequently asked questions about Chicago Outdoor activities

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

One of the best things we did was take this boat tour while visiting Chicago for the first time. You will learn so much interesting facts about Chicago and it’s amazing to see the city in a different view. I highly recommend dressing for the weather. It can get windy and cold so bring a jacket and sunglasses if it’s sunny.

Guide was excellent. Very interesting tour. We missed our original tour and had to take the next tour which was longer and probably better because we weren’t areas that the shorter tour would not have take. Us.

Awesome tour with an awesome guide ! Baylor’s enthusiasm and friendliness really sold it and she even managed to give me goosebumps with the way she told some of the stories! :)

Our guide Ty was super cool and handled the whole tour well. I'll definitely tell all my friends who visit Chicago to take this tour.

Conor was very knowledgeable and the tour was a great pace with lots of info!