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How to Spend 2 Days in Chicago

How to Spend 2 Days in Chicago

Whether spending a weekend in the Windy City or planning a midweek adventure, you have plenty of time to discover Chicago’s highlights in two days. From world-class museums and world-ranking skyscrapers to the city’s delectable dining scene, here’s how to make the most of your 2-day stay.

 

Day 1: The Loop and Beyond

Morning: Set right along the waterfront, Chicago’s Museum Campus (home to the Field Museum of Natural History, the Adler Planetarium, the Shedd Aquarium, and more) is the perfect place to immerse yourself in the Windy City’s cultural side.

 

Afternoon: The Loop, Chicago’s downtown business district, is home to a heavy concentration of landmarks. The neighborhood is ideal terrain for walking tours—explore on foot and stumble across highlights ranging from Millennium Park and the Willis Tower (formerly the Sears Tower) to public sculptures by Pablo Picasso and Alexander Calder.

 

Night: Head up to the top of the Willis Tower, where you can enjoy a multicourse meal while taking in views of Chicago lit up after dark. Alternatively, a dinner cruise along Lake Michigan combines gourmet dishes with splendid skyline views.

 

Day 2: Sand and Surf, Snacks and Sightseeing

Morning: On Chicago’s 26-mile (42-kilometer) shoreline, admire what might look to be the ocean—a stretch of Lake Michigan often called the “Third Coast.” When the sun’s out, follow Chicagoans to the lake’s sandy beaches, from North Avenue Beach to Oak Street Beach. Alternatively, enjoy waterside attractions of a different kind at Navy Pier.

 

Afternoon: Complete this day with a food tour of Chicago’s vibrant culinary culture. Seek out hot dogs and Italian beef sandwiches, and save extra room for deep-dish pizza. A number of renowned, decades-old pizza joints can be found right in the Loop, from Lou Malnati’s and Giordano’s to Gino’s East.

 

Night: When the sun is setting, embark on a helicopter tour and get rewarded with a unique, aerial perspective of the city. Spot Chicago’s most distinctive skyscrapers, discover its different neighborhoods from the air, and see the lights come on as evening descends.

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19 Tours and Activities

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Chicago Architecture River Cruise

Chicago Architecture River Cruise

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Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD46.87
From
USD46.87

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

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996
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
USD44.99
From
USD44.99

Lake Michigan Sightseeing Cruise
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Lake Michigan Sightseeing Cruise

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349
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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  • 40 minutes
  • Free Cancellation
From
USD28.34
From
USD28.34

Chicago Signature Dinner Cruise on Lake Michigan
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Chicago Signature Dinner Cruise on Lake Michigan

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141
Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
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  • 3 hours
From
USD122.80
From
USD122.80

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship
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Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

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Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
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  • 1 hour 15 minutes
  • Free Cancellation
From
USD49.00
From
USD49.00

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

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Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.
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  • 45 minutes
  • Free Cancellation
From
USD849.00
per group
From
USD849.00
per group

Chicago Favorites Ultimate Food & Walking Tour

Chicago Favorites Ultimate Food & Walking Tour

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384
Stroll through downtown Chicago on this walking food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, plus chocolates and pastry. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. Upgrade your tour to include three pours of local craft beer.
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  • 3 hours
  • Free Cancellation
From
USD74.99
From
USD74.99

Chicago CityPASS

Chicago CityPASS

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Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Shedd Aquarium, Skydeck Chicago, and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.
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  • 9 days
  • Free Cancellation
From
USD114.00
From
USD114.00

30 Minute Lake Michigan Speedboat Ride

30 Minute Lake Michigan Speedboat Ride

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126
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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  • 30 minutes
From
USD34.75
From
USD34.75

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

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167
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 4 hours
  • Free Cancellation
From
USD27.00
From
USD27.00

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

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Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
From
USD89.99
From
USD89.99

Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

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490
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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  • 2 to 4 hours
  • Free Cancellation
From
USD39.95
From
USD39.95

Underground Donut Tour: Chicago's First Donut Tour
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Underground Donut Tour: Chicago's First Donut Tour

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Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and vegan, gluten-, and nut-free options are also available.
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  • 2 hours
  • Free Cancellation
From
USD40.00
From
USD40.00

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

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The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
USD65.00
From
USD65.00

Chicago Lakefront and Museum Campus Small Group Tour

Chicago Lakefront and Museum Campus Small Group Tour

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156
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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  • 2 hours
  • Free Cancellation
From
USD76.48
From
USD76.48

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

Chicago Architecture Walking Tour: Dazzling Interiors™ of the Loop

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337
See the overlooked highlights of Chicago’s Loop district with a 2-hour walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially-designed route with an experienced guide. Learn about the city’s architecture, art and history while visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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  • 2 hours
  • Free Cancellation
From
USD35.00
From
USD35.00

Chicago's Ultimate City Bike Tour
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Chicago's Ultimate City Bike Tour

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58
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
From
USD54.99
From
USD54.99

Bike Tour of Chicago's Lakefront Neighborhoods
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Bike Tour of Chicago's Lakefront Neighborhoods

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151
Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
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  • 3 hours
  • Free Cancellation
From
USD54.99
From
USD54.99

Chicago Loop Secret Food Tour with Private Tour Option

Chicago Loop Secret Food Tour with Private Tour Option

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264
Explore Chicago's buzzing food scene with a small group on this small group walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste classic Chicago foods, from deep-dish pizza to dipped Italian beef sandwiches.
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  • 3 hours
From
USD84.53
From
USD84.53