Millennium Park
Home to the iconic 'Cloud Gate' (The Bean) and Crown Fountain, this park is a must-see for its public art and vibrant atmosphere.
Good to know
Arrive early in the morning for fewer crowds, especially if you want photos with The Bean.
What this plan covers
This itinerary is designed for first-time visitors eager to experience Chicago's most famous landmarks and essential attractions. From architectural marvels to deep-dish delights, it offers a comprehensive taste of the city's unique charm and energy, perfect for those seeking a memorable urban adventure.
Sightseeing 2
Culture 2
Activity 3
Food 3
Nature 2
Shopping 1
Viewpoint 2
Day 1
Millennium Park, Art Institute of Chicago and 3 more
See the day
Day 2
Field Museum, Grant Park and 3 more
See the day
Day 3
Willis Tower Skydeck, Chicago Board of Trade Building and 3 more
See the dayOpening hours, prices and routes can change, so check the details before you set off.
Day 1
Art Institute of Chicago
Explore one of the oldest and largest art museums in the United States, boasting an extraordinary collection spanning centuries and continents.
Good to know
Consider purchasing timed-entry tickets online in advance to secure your preferred entry time and avoid queues.
Chicago Riverwalk
Stroll along this scenic pedestrian path offering stunning views of Chicago's renowned architecture from a unique perspective.
Good to know
Many boat tours depart from here; check departure points if you plan a cruise.
Chicago Architecture Foundation Center River Cruise
Gain unparalleled insight into Chicago's architectural heritage on a critically acclaimed boat tour, a quintessential first-timer experience.
Good to know
Book tickets well in advance, especially during peak season, as tours often sell out quickly.
Deep Dish Pizza Dinner
Savor Chicago's most famous culinary invention, a hearty deep-dish pizza, for an authentic taste of the city.
Good to know
Be prepared for a wait at popular establishments like Lou Malnati's or Giordano's, or order ahead for pickup.
Day 2
Field Museum
Delve into natural history with Sue, the most complete T-Rex skeleton, and world-class exhibits on ancient cultures and biodiversity.
Good to know
Located on Museum Campus, it's easily accessible by public transit; consider a CityPASS if visiting multiple museums.
Grant Park
Explore 'Chicago's Front Yard,' a vast urban park featuring Buckingham Fountain and connecting the Museum Campus to the city center.
Good to know
Wear comfortable shoes for walking, as the park covers a large area perfect for a leisurely stroll.
Magnificent Mile (Michigan Avenue)
Experience world-class shopping, impressive architecture, and luxury hotels along Chicago's premier commercial district.
Good to know
Explore the side streets for hidden gems and dining options beyond the main thoroughfare.
360 Chicago Observation Deck (John Hancock Center)
Enjoy breathtaking panoramic views of the city skyline, Lake Michigan, and neighboring states from 1,000 feet up, with the thrilling 'TILT' experience.
Good to know
Consider visiting at sunset for spectacular views as the city lights up; book tickets online for convenience.
Dinner in River North
Discover River North's vibrant dining scene, offering a diverse array of acclaimed restaurants and lively nightlife options.
Good to know
Reservations are highly recommended for popular restaurants, especially on weekends.
Day 3
Willis Tower Skydeck
Ascend to the top of the Western Hemisphere's second-tallest building for unparalleled views and the exhilarating 'Ledge' glass boxes.
Good to know
Go early in the morning right after opening to minimize wait times for both the elevator and The Ledge.
Chicago Board of Trade Building
Admire the stunning Art Deco architecture of this historic landmark, a symbol of Chicago's financial prowess.
Good to know
Best viewed from the street level; combine with a walk through the surrounding Financial District.
Lincoln Park Zoo
Visit one of the last free zoos in the United States, home to a diverse collection of animals set within a beautiful urban park.
Good to know
Entry is free; check the zoo's website for any special exhibit times or seasonal events.
Lincoln Park Conservatory
Step into a lush, tranquil oasis featuring exotic plants and beautiful floral displays, a perfect escape from the urban bustle.
Good to know
Located adjacent to the Lincoln Park Zoo, making it easy to visit both attractions together.
Dinner in Old Town
Experience the charming, historic ambiance of Old Town, known for its Victorian architecture, unique boutiques, and diverse dining options.
Good to know
Explore Wells Street for a variety of restaurants, from casual eateries to upscale dining.
Where to stay
Hotels in Chicago
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Things to book
Tours and activities in Chicago
Guided tours, day trips and tickets to book alongside your stay.
Standard tour
Milwaukee,Miller Brewery Tour&Tasting 1-Day Tour from Chicago
Free cancellationFind deals
Standard tour
Oktoberfest Walking Brewery Tour in Malt Row
Free cancellationFind deals
Activity tour
Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class
Free cancellationFind deals
Standard tour
Night Time Bayou Booze Cruise
Free cancellationFind deals
Standard tour
2 Hour-Date Night & Sunset Cruise.
Free cancellationFind deals
Activity tour
New Orleans Fishing Charter (ClearVision Charters)
Free cancellationFind deals
Activity tour
New Orleans Fishing Charter
Free cancellationFind deals
Activity tour
New Orleans Private Fly Fishing (ClearVision Charters)
Free cancellationFind deals
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Other ways to spend a few days in Chicago, from our own travel research.
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