Top Chicago Day Trips

19 results

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

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4.7

(9,897)

Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

from $45

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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4.4

(907)

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

from $33

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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4.8

(16,005)

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

from $39

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

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4.7

(3,148)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

from $28

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.

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4.3

(9)

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

8 to 10 hoursFree Cancellation

from $125

Likely to Sell Out

Escape the city and discover the serene beauty of the Midwest on this full-day Lake Geneva and Anderson Japanese Gardens tour from Chicago. Start your journey with a relaxing lakeside stroll through Lake Geneva, where historic estates and tranquil waters await. Enjoy optional boat rides and scenic views before heading to the renowned Anderson Japanese Gardens. There, immerse yourself in a peaceful 12-acre oasis featuring koi ponds, waterfalls, and traditional Japanese landscaping. Unlimited Bottled Water & Complimentary Snacks – Stay refreshed and energized throughout the journey. Themed Attractions with Seasonal, Adventurous & Playful Highlights – Carefully selected for excitement and discovery. Happy Family Time – Kids enjoy 50% off for a joyful and budget-friendly trip in July and August.(Prices shown are the final specials) Exclusive Travel Keepsakes – Includes a custom travel passport and share-worthy moments for your social media.

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Lake Geneva, Anderson Japanese Gardens 1 Day Tour From Chicago

7 to 9 hoursFree Cancellation

from $126

Discover the creative side of Chicago beyond the city limits with this small-group tour of suburban hidden gems! Visit charming historic districts, offbeat local landmarks, striking public art, scenic waterfronts, and under-the-radar eateries as your expert guide shares insider stories you won’t find in guidebooks. With transport included and group size kept small, it’s a relaxed, camera-worthy way to explore unique neighborhoods, architectural treasures, and distinctive local culture. Ideal for repeat visitors, adventure seekers, or anyone curious to see more than the Magnificent Mile.

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5.0

(4)

Chicago Suburbs Hidden Gems: Small-Group Exploration Tour

9 hoursFree Cancellation

from $199

Likely to Sell Out

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable car ride for breathtaking views. Continue to Galena, a beautifully preserved historic town where 80% of the buildings are listed on the National Register of Historic Places. Here, you’ll visit the Ulysses S. Grant Home and take in the serene beauty of Grant Park. With a total travel distance of 325 km from Chicago, this tour offers the perfect blend of history, scenery, and relaxation before heading back to the city.

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One Day Galena and Dubuque Tour from Chicago

6 to 7 hoursFree Cancellation

from $395

Special Offer

4.6

(3,297)

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

from

$42

$49

Set sail for an unforgettable experience on the water with private boat tours and captained rentals along the Chicago River and Lake Michigan. Whether you're looking to explore the city’s historic waterways or enjoy a relaxing cruise with skyline views, we’ve got you covered. Cruise past iconic landmarks like the Wrigley Building on the Chicago River before heading out to Lake Michigan, where you'll take in panoramic views of the city’s world-famous skyline. With a comfortable and stylish cruiser boat, every ride is smooth, scenic, and uniquely Chicago. Want a custom experience? Choose a private boat rental with a licensed captain—ideal for birthdays, date nights, family outings, or simply relaxing with friends. You enjoy the moment, and we handle the navigation. No boating experience needed. Just bring your favorite snacks, drinks, and good vibes—we’ll provide the boat, the captain, and the unforgettable views. Book now and experience Chicago like never before—from the water!

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4.4

(7)

Chicago City Boat Tours

2 to 8 hoursFree Cancellation

from $299

Per group

Likely to Sell Out

4.7

(2,320)

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

from $45

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

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3.9

(2,234)

Hop-On Hop-Off Sightseeing Tour by Open-top Bus

2 hoursFree Cancellation

from $49

Total Chicago: From Architecture to Food

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

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4.9

(1,218)

Chicago in a Day: Food, History & Architecture Walking Tour

4 hours 30 minutesFree Cancellation

from $101

Price varies by group size

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

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4.9

(561)

Chicago City Minibus Tour

2 hoursFree Cancellation

from $50

Likely to Sell Out

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

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Chicago-Milwaukee Small Group Tour

6 to 7 hoursFree Cancellation

from $415

Likely to Sell Out

Escape the city for a day of Dutch-inspired adventure in Michigan! Journey from Chicago to Holland’s Windmill Island Gardens, home to vibrant tulip fields (in season), a real 250-year-old windmill, and charming European-style village sights. Your bilingual guide leads the way with family-friendly stories, unlimited bottled water, complimentary sweet treats, and exclusive travel keepsakes. Enjoy time to stroll gardens, ride the Saugatuck dunes, and explore Holland Village’s history—all with special savings for kids. The perfect one-day escape for families, photography lovers, and tulip fans!

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4.5

(4)

Windmill Island Gardens Day Tour from Chicago – Kids Save 50%

10 to 11 hoursFree Cancellation

from $99

Likely to Sell Out

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.

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Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

9 to 10 hoursFree Cancellation

from $1,200

Per group

Likely to Sell Out

Escape Chicago for a day and experience the Midwest’s small-town charm on a guided tour to Galena and Dubuque. Stroll the Mississippi River in Iowa’s oldest city, explore Galena’s 19th-century streets and landmarks, and visit the Ulysses S. Grant Home. Enjoy lively commentary, unlimited bottled water, complimentary snacks, and curated family-friendly stops. Capture exclusive travel keepsakes and take advantage of special discounts for kids in July and August. Perfect for history lovers, families, and anyone seeking a scenic day beyond the city.

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Galena Day Tour from Chicago: Historic Sites and River Views

8 to 10 hoursFree Cancellation

from $126

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, history, and architecture. Start by marveling at Chicago’s world-renowned skyline, exploring its legendary landmarks, and soaking in the vibrant energy of the city. Then, step beyond the usual tourist path to uncover the hidden treasures nestled in the suburbs. Discover the BAPS Shri Swaminarayan Mandir, an architectural masterpiece showcasing intricate carvings and spiritual serenity; visit the quirky Leaning Tower of Niles, a charming replica of Italy’s famous landmark; experience the awe-inspiring Bahá’í House of Worship, known for its breathtaking design and peaceful ambiance; and stroll through Westfield Old Orchard, a stylish open-air shopping destination offering a blend of modern luxury and relaxed charm. This thoughtfully curated journey bridges the gap between city excitement and suburban surprises. Ready to explore?

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Chicago City's Iconic Sights and Suburb Gems Tour

5 to 10 hoursFree Cancellation

from $159

Top Attractions in Chicago

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Chicago’s many attractions can keep you busy, but there’s plenty to see beyond the Windy City’s borders. Guided Chicago day trips visit nearby cities like Milwaukee with its beer brewing heritage and cultural sites, tour the Chicago suburbs’ quirky attractions, or head to nearby Oak Park to view a collection of Frank Lloyd Wright homes. In spring, you can visit Michigan's tulip festivals and windmill displays. Whether you're interested in regional history, architectural innovation, or natural scenery, these day trips expand on your Chicago experience.

Top Chicago Day Trips

19 results

Top Attractions in Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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