Do you have an upcoming trip to Chicago, but you only have a day or two to explore? Not to worry! You can easily see a lot of Chicago in just a few hours. However, it can be daunting to sift through all of the activities and attractions, especially if you’re a first-time visitor. We’ll help you narrow down the top things to see in Chicago during your limited stay and share a couple suggested itineraries. When in doubt, a biking or walking tour is an excellent way to see a lot of the city in a short amount of time!
Is a Half Day Enough to See Chicago?
Even if you only have a few hours to see the city, you can still experience a variety of Chicago’s highlights, including world-famous landmarks and local eats. Many of the city’s main attractions are close together and easy to access via public transit or bike, making Chicago the perfect place for a quick visit. In addition, many sites are free and/or don’t require a ticket in advance, so they can be seen quickly. Here are some of the top landmarks to see downtown in a short amount of time:
Downtown & Lakefront Highlights
Millennium Park/The Bean
No trip to Chicago is complete without visiting Millennium Park’s world-famous bean-like sculpture, otherwise known as the Cloud Gate. The park itself has a variety of things to see, including:
- Crown Fountain – This unusual fountain consists of two 50-foot glass brick sculptures that contain LED screens. These screens project the faces of a thousand or so Chicagoans, which will intermittently “spit” water.
- Pritzker Pavilion – Designed by Frank Gehry, this outdoor amphitheater hosts a variety of events throughout the summer, including movie nights and concerts.
- Lurie Garden – This is a small, 2.5-acre naturalistic garden filled with native prairie grasses and wildflowers.
Buckingham Fountain
Located in the heart of Grant Park, Buckingham Fountain is a massive wedding cake-style fountain modeled after the Latona Fountain in the gardens of Versailles. At the time of its completion in 1927, it was the largest fountain in the world. The location also provides panoramic views of the skyline, and it’s in walking distance from Millennium Park.
Pro Tip💡: Join Chicago’s Ultimate City Bike Tour to see Millennium Park, Buckingham Fountain, Museum Campus, and more in just three hours!
Willis Tower
To truly see the entire city in just a few minutes, visit the Skydeck at Willis (better known as Sears) Tower. From there you can take in 360-degree views of the skyline and witness the endless expanse of Lake Michigan.
Chicago Riverwalk & Architecture
The Chicago Riverwalk is about a 1-mile path along the river lined with bars and restaurants. If you want to marvel at the city’s architecture, this is the perfect place to see some of Chicago’s most iconic buildings, including the Wrigley Building, Marina City, and the Merchandise Mart. If you’re able to visit at night, be sure not to miss ART on THE MART, a digital art show projected on the side of the Merchandise Mart.
Chicago Must-Eats
To complete your short-term Chicago experience, you need to try at least one of Chicago’s iconic foods: deep dish pizza, a Chicago-style hot dog, and/or an Italian beef sandwich. These iconic foods are all must-eats in Chicago for first-time visitors.
Lou Malnati’s is excellent for deep dish pizza, and there are multiple locations downtown. This makes it a convenient choice no matter where you’re staying.
Pro Tip💡: Visit around lunchtime (11 a.m. to 3 p.m.) to avoid a wait for a table, as the restaurants tend to get busy during dinner. Do note, deep dish pizza takes about 45-minutes to bake no matter the time of day, so it’s not a quick meal.
For a Chicago-style hot dog, you can find a hot dog stand almost anywhere downtown. In fact, there are more hot dog stands in the city than McDonald’s, Wendy’s, and Burger King restaurants combined.
In terms of an Italian beef sandwich, Al’s #1 Italian Beef is an excellent choice. There’s a reason it has “#1” in its name. Be sure to order your sandwich wet with sweet peppers and giardiniera for the ultimate experience.
If you just want a quick snack, Garrett’s Popcorn is the perfect treat, and it’s a fan-favorite souvenir to bring home to friends and family! To make the most out of a half-day in Chicago and to knock all of these items off of your list in just three hours, check out Bobby’s Bike Hike’s Chicago Favorites Food & Walking Tour.
What Can You See In a Full Day?
If you have a full day in Chicago, you can take your time exploring more of the city. Consider getting out of downtown and visiting a neighborhood or two, or dedicating time to peruse a museum. No matter your interests, Chicago has something to suit everyone’s fancy.
Iconic Landmarks
Navy Pier
Navy Pier is one of Chicago’s top tourist attractions. You could easily spend a couple hours here, but a quick trip is possible as well! Here you will find a food court, amusement attractions like the Centennial Wheel and Flyover Chicago, and it’s the perfect place to pick up a couple souvenirs. If you have a little extra time, you can check out the beer garden near the end of the pier, or see if there’s a show playing at the Chicago Shakespeare Theatre.
Wrigley Field
Even if you’re not a baseball fan, Wrigley Field is a historic site that carries a lot of significance for the city. Located north of downtown, the stadium is easily accessible by taking the Red Line train to Addison.
Lincoln Park Zoo
The Lincoln Park Zoo is a free attraction in Chicago’s Lincoln Park Neighborhood. This zoo features nearly 200 species of animals from around the globe, making it a great place to spend an hour or two and learn about the world’s fauna. You can also get a glimpse of the zoo along our Lakefront Neighborhood’s Bike Tour.
Neighborhood Exploration
Speaking of neighborhoods, with a full day in Chicago you can trek out of downtown to explore a few of the city’s distinct communities.
Wicker Park
If you’re looking for a cozy day out and about, visit Wicker Park to peruse its collection of cafes, record shops, and book stores along Milwaukee Avenue. This western neighborhood is convenient to get to by taking the Blue Line train north to the Damen stop.
Chinatown
Known for its authentic, diverse range of food, Chicago’s Chinatown is full of amazing restaurants, rich culture, and unique shops. Take the Red Line train south to Cermak/Chinatown to delve into everything the neighborhood has to offer. If you’re unsure about which restaurant(s) to try, check out this guide to Chinatown’s incredible food scene!
West Loop
Chicago’s West Loop had a long history as an industrial and meatpacking hotspot, but today it’s a thriving area with some of the best restaurants in the world, with many earning a Michelin Star and/or James Beard Award. The West Loop—specifically Fulton Market—is one of the first stops along our Westside Foodie Ride Bike Tour if you want to see this and other western neighborhoods within a few hours.
Cultural Stops
Museum Campus
On the southern end of downtown, Museum Campus is home to three of Chicago’s major museums: the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. It would take a couple days to explore all three, but it’s worth it just to walk around the area and take in the skyline views.
Art Institute of Chicago
Housing around 300,000 pieces of art, the Art Institute of Chicago is the second largest art museum in the United States. In addition, this museum has one of the largest collections of French Impressionist artwork outside of France, including paintings by Monet, Renoir, Degas, Morisot, and more. To properly see all of the exhibits you need to spend at least three hours here, however the museum provides a guide that details the most popular pieces of art that you can see within one hour if you’re on a time crunch.
Chicago Cultural Center
Originally the main branch for the Chicago Public Library system, the Cultural Center is now an exhibition space and popular venue for various events such as weddings and city receptions. Entrance is free, and it’s worth a quick stop to check out the rotating exhibitions and see the intricate Tiffany glass dome, which is the largest in the world. The dome spans 38 feet in diameter and is made of more than 30,000 pieces of glass.
Pro Tip💡: Rent a bike to get around the city quickly!
Sample Chicago Itinerary
Half-Day Itinerary Example:
- Start: Millennium Park + Cloud Gate
To kick off your half-day in Chicago, stop by Millennium Park to check off one of the most popular sites in the city: The Bean. Be sure to take a selfie in the sculpture’s reflection. You can quickly explore the entire park in less than 15-20 minutes.
- Explore the Chicago Riverwalk
Following your Millennium Park adventure, walk north on Michigan Avenue to the riverwalk. This mile-long stretch allows you to take in some of the city’s most breathtaking architecture and enjoy a unique perspective of Chicago from river level. Walking the entire length of the riverwalk takes about 20 minutes one way.
- Stop for a deep dish lunch
For lunch, stop by Lou Malnati’s to try authentic deep dish pizza. The restaurant opens at 11 a.m., and there’s a location in the Wrigley building on the opposite side of the river, making it a convenient place to grab a meal downtown.
- Bike the Lakefront Trail
A 15-minute walk from Lou Malnati’s, you can rent a bike from Bobby’s Bike Hike and traverse the Lakefront Trail. This paved path spans a total of 18.5 miles, but many just bike a few miles north toward Lincoln Park or south to Museum Campus to enjoy the refreshing breeze and the blue expanse of Lake Michigan.
- End with a skyline view from Navy Pier
After enjoying the scenery along the Lakefront Trail, stop at Navy Pier near Bobby’s Bike Hike to indulge in the amusement rides and take in one last view of the city’s skyline.
Full-Day Itinerary Example:
- Morning: Bobby’s Bike Hike tour to see top landmarks
If you have a full day in Chicago, start with a bike tour to see the city’s most popular sites in just a few hours. A bike tour helps avoid the hassle of walking or taking public transit from place to place, and you get to learn about each site along the way. Try the Ultimate City Bike Tour to explore downtown, or hop on the Bikes, Bites, & Views tour to see Wrigleyville and Lincoln Park while filling your stomach with Chicago’s famous foods and local craft beer.
- Afternoon: Museum Campus or Art Institute
Chicago’s major museums each require at least a couple hours to explore, so you will likely only have time for one. The most accessible museums from downtown include the Art Institute of Chicago, the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. So, choose the museum that best fits your interests!
Note: Double check your chosen museum is open on the day you plan to visit.
- Evening: Dine in Chinatown
Chinatown has some of the best food in the city. This thriving neighborhood is filled to the brim with shops and restaurants serving Sichuanese food, hot pot, dim sum, Hong Kong-style BBQ, you name it. If you’re overwhelmed by the amount of restaurant options, consider joining a food and walking tour of Chinatown to find some of the best eats. Also, be sure to check out the Chinese American Museum of Chicago if you have extra time.
Pro Tip 💡: When planning your Chicago itinerary, consider finding a hotel in downtown neighborhoods like The Loop or along the Magnificent Mile to minimize travel time.
Which Chicago Tour is Right for You?
Interested in taking a tour to make the most out of a short visit to Chicago? Let’s help you decide which option(s) fit your travel style, pace, and priorities:
Foodie
- Westside Foodie Bike Ride: This tour only runs Friday through Sunday during the summer, but it’s an excellent tour to sample a diverse range of foods and to see a few of the city’s vibrant neighborhoods outside of downtown. You cover a lot of ground, but the tour stays at a leisurely pace.
- Chicago Favorites Food & Walking Tour: If you want to sample Chicago’s staple foods, this is the tour for you. You’ll get a slice of deep dish pizza, a Chicago-style hot dog, and half of an Italian beef sandwich, along with a couple desserts! The route is about 1.5 to 2 miles.
- Chinatown Food & Culture Walking Tour: To truly experience Chinatown, you need to dine at a few of the restaurants. This tour allows you to try five food samples from different regions of China, including Canton, Sichuan, and Xi’an. You’ll discover how diverse Chinese food is and hear the history behind Chicago’s Chinatown. Come hungry and ready to learn.
Adventure Seeker
- Chicago’s Ultimate City Bike Tour: To see Chicago’s top downtown attractions in just three hours, this is the best tour to do. This non-food bike tour takes you to the Chicago River, Millennium Park, Buckingham Fountain, Museum Campus, and more. Along the way you’ll learn the essential history of Chicago from the origin of its name to present day. The route is only about 9 miles, however it does encounter a few hills, so be ready to get some exercise.
- Bikes, Bites, & Views (AM tour): Our longest and most popular bike tour, the 4.5-hour Bikes, Bites, & Brews takes you about 14 miles through Chicago’s northern neighborhoods and lets you sample deep dish pizza, a Chicago-style hot dog, a dessert, and local craft beers. It’s the perfect mix of food, biking, and sightseeing. If that’s not enough to convince you, this tour was rated a Top 20 Food Tour in the World by TripAdvisor!
Family-Friendly
- Family & Food Bike Tour of Top Attractions: Visiting Chicago with young kids? This tour is perfect for families wanting to bike around and sample some of Chicago’s famous foods. You’ll get deep dish pizza, a Chicago-style hot dog, as well as a dessert while learning about the city and biking through downtown Chicago.
- Lakefront Neighborhoods Bike Tour: This 3-hour bike tour is an incredibly easy ride through Chicago’s northern neighborhoods, including Lincoln Park, Old Town, and the Gold Coast. On this tour you get to take a peak at the animals in Lincoln Park Zoo, see a church that survived the Great Chicago Fire, and visit a park inspired by “The Wizard of Oz”. This flat, 8-mile tour is excellent for people of all ages.
Pro Tip💡: Bobby’s Bike Hike offers a variety of child equipment, so kids of any age can come along, even if they don’t know how to ride a bike!
FAQs
- Is a half-day tour enough to see Chicago?
Yes! While you won’t be able to visit all of the top sites, you can see a decent amount thanks to the city’s compact layout and convenient public transit system.
- What’s included in a full-day Chicago tour?
Our 5-hour One Day in Chicago Food & Highlights Walking Tour consists of 5 food samples, including deep dish pizza, a Chicago-style hot dog, and an Italian beef sandwich, as well as an exquisite tour guide to walk you around both the iconic and hidden sites of downtown. See the stunning Holy Name Cathedral, Millennium Park, the world’s largest Tiffany glass dome, the Chicago Theater, and much more. You also get a free 2-hour bike or kayak rental, so you can continue to explore the city at your leisure!
- How many days should I spend in Chicago?
Ideally, budgeting 3 days allows you time to see some of the top sites, sample Chicago’s food scene, and explore a neighborhood or two. However, you can see a lot of the city in just one day!
- What is the best time of year to visit Chicago?
Peak season in Chicago is from late-May to early-September, however one of the best times to visit the city is after Labor Day until Mid-October. At this time, attractions are typically a little less crowded and the weather is usually still warm.
Things to Know / Expect
- Crowds: Tourism to Chicago has grown rapidly the past few years, so anticipate crowds at top sites during peak season, especially June through August. Make reservations and buy tickets for attractions in advance.
- Weather: Weather in the Midwest can be unpredictable no matter the time of year, so be sure to check the weather forecast prior to your trip. That being said, summers are usually hot and humid, and winters are cold and blustery. Pack accordingly!
- Traffic: Traffic in the city gets busy around rush hours (7-9 a.m., 4-6 p.m.), so plan to arrive at your destination early if traveling during those times, or take the train. Driving in Chicago is not recommended as parking is expensive and traffic can easily become congested.
- Transit: Chicago’s public transit system makes it incredibly easy to get almost anywhere in the city. It’s relatively inexpensive and easy to navigate. For more information on transit around Chicago, check out this blog.
- Biking Safety: Chicago is generally considered bike-friendly, providing many bike lanes through the city streets. In addition, you can utilize the car-free Lakefront Trail to easily travel north and south. However, always exercise caution and don’t bike on sidewalks.
- What to bring on a tour: Bring a bottle of water, your ID (in case you plan to purchase alcoholic beverages), and comfortable clothing/shoes.
Conclusion
Whether you’re on a tight schedule or have a full day or more to explore, Chicago offers something for every traveler. To make the most of your time and see the city like a local, consider booking a tour with Bobby’s Bike Hike to reduce the hassle of planning and let us show you around this beautiful city!
