Ideas for One Day Trip to Chicago in 2024
Only textLiving near the North Shore of Chicago has its perks, especially when planning a day trip into the city. Whether you’re with family, friends, or on a solo adventure, Chicago is full of activities that cater to every interest and age group. So, whether it’s your first visit or you’re a local looking for something new, here’s a guide to some of the best day trip ideas in Chicago, perfect for everyone from first-time visitors to seasoned Chicagoans.
Why Visit Chicago?
Chicago isn’t just any city; it's the third largest city in the United States and a vibrant place with a rich history, stunning architecture, and a diverse choice of attractions. From iconic landmarks like the Willis Tower and Millennium Park to hidden gems in its many unique neighborhoods, there’s always something new and exciting to explore.
The city is a hub of arts and culture, offering world-class museums like the Art Institute of Chicago and the Field Museum. Outdoor enthusiasts can enjoy the beautiful parks like Grant Park and Maggie Daley Park, lakefront trails, and boat tours. Foodies will find a culinary paradise with everything from deep-dish pizza to gourmet dining experiences. Simply put, Chicago has it all, and there's never a dull moment when you're exploring this beautiful city.
FAQs About Traveling to Chicago
As a Chicago native, I get tons of questions about traveling to the big city. Here's the top questions I get about taking a short trip to Chicago:
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Absolutely! Downtown Chicago, known as The Loop, is incredibly walkable. You can easily explore the city's top attractions like Millennium Park, Navy Pier, and the Chicago Riverwalk by foot. Everything is close by, making it a breeze to navigate without a car. Plus, the area is well-served by public transportation, including the “L” train and buses, so getting around is super convenient. Whether you’re checking out the stunning architecture, enjoying outdoor activities, or visiting museums, downtown Chicago is perfect for pedestrians.
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Chicago is famous for its unique and delicious food scene. When you’re in the Windy City, you have to try the deep-dish pizza. This thick, hearty pizza has layers of cheese, toppings, and a chunky tomato sauce that’s baked to perfection. Another must-eat is the Chicago-style hot dog, an all-beef frank topped with mustard, onions, relish, a pickle spear, tomatoes, sport peppers, and celery salt, all in a poppy seed bun. And for dessert, indulge in a rich and creamy slice of Chicago-style cheesecake. These dishes are iconic and give you a true taste of Chicago’s vibrant culinary culture.
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The top tourist attraction in Chicago has to be Millennium Park, especially its famous sculpture, Cloud Gate, affectionately known as "The Bean." Located in the heart of downtown, Millennium Park draws millions of visitors every year with its impressive public art, beautiful gardens, and free cultural events. It’s part of the larger Grant Park, which runs along Lake Michigan, offering tons of space for outdoor activities, live music, and seasonal events. Its central location makes it a fantastic starting point for exploring all that Chicago has to offer.
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The Magnificent Mile, also known as North Michigan Avenue, is a must-visit spot in Chicago. It's definitely the most popular with all mainstream shops.
It's a stretch that runs from the Chicago River to Oak Street, packed with high-end shops, dining options, and plenty of entertainment. The Magnificent Mile has it all. You'll find everything from luxury boutiques and department stores to iconic architectural gems like the Wrigley Building and the John Hancock Center.
It's the perfect place to soak up some Chicago charm and excitement, whether you're a visitor or a local.
If you're looking for some more local flair, I highly suggest heading to Damen & Milwaukee in Wicker Park and Southport Corridor (located at Addison & Southport) in Lakeview.
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Chicago has a great public transportation system. The Chicago Transit Authority (CTA) runs the “L” trains and buses that cover nearly every part of the city.
You can easily hop on these to get to top spots like Millennium Park, the Art Institute of Chicago, and Navy Pier. For convenience, grab a Ventra Card, which works on both buses and trains.
If you prefer flexibility, rideshare services like Uber and Lyft are everywhere and super convenient.
For a more active approach, renting a bike from the Divvy bike-share program is fantastic, especially if you want to explore the beautiful lakefront and neighborhoods.
Chicago’s downtown, known as The Loop, is highly walkable, so it’s easy to stroll between attractions like the Chicago Riverwalk, Willis Tower, and Grant Park.
For trips a bit further out, like to the Field Museum or Shedd Aquarium, I recommend rides share choices as they are far from the train stops.
The Metra trains are your best bet for quick access to the suburbs and other outlying areas if you're not driving. Once you get to the suburbs though, you'll most likely need a car.
If you drive, explore the app SpotHero to find inexpensive parking around the city. Navigating street signs can be tricky if you're not used to it!
Fun Ideas for a Day Trip to Chicago
There is no shortage of options when planning a one-day Chicago itinerary. You won't be able to squeeze all of the ideas on this list into one day, but any of these fun activities will make your short trip to the Windy City a memorable one!
Outdoor Things to Do in Chicago
Visit the Bean
It was recently redone. No trip to Chicago is complete without a visit to Millennium Park to see "The Bean." This iconic sculpture is a perfect place for photos and people-watching.
There are restaurants right across the street and it’s a short walk to Maggie Daley Park. Plus, in the winter months, you can ice skate!
The park also hosts free outdoor activities and live music during the summer months, making it one of the best places to soak up the Windy City vibe.
Millennium Park Music in the Par
Millennium Park’s Summer Music Series is a must-do, offering a variety of free concerts ranging from jazz to classical to indie rock. Imagine relaxing on the Great Lawn with the Chicago skyline as your backdrop, listening to live music. Pack a picnic and soak up the atmosphere. For more information, visit the Millennium Park website.
Maggie Daley Park
Next to Millennium Park, Maggie Daley Park is an adventure goldmine with three separate play areas. You can ice skate here in the winter and enjoy numerous trails for walking. The park is free, making it a great budget-friendly option. Pack a picnic and soak in the beautiful scenery.
Lincoln Park Zoo, Free!
Another fantastic free activity for the whole family is the Lincoln Park Zoo, perfect for a leisurely stroll. The zoo's manageable size makes it easy to explore, and the nearby Lincoln Park Conservatory offers additional educational fun. Visit around 10 a.m. when the animals are most active.
Lake and River Boat Tours
For a unique perspective on the Windy City, take a lake or river boat tour. These tours are great for learning about Chicago’s history and architecture while enjoying the outdoors. Don’t forget sunscreen and hats for a sunny day.
Green City Lincoln Park Farmers Market
The Green City Market in Lincoln Park is a wonderful seasonal activity. Hosted on Saturdays and Wednesdays, it’s a great place to learn about local produce and sustainability. Live music and cooking demonstrations make it both educational and fun.
Logan Square Farmers Market
Similar to the Green City Market, the Logan Square Farmers Market offers a vibrant community-focused experience every Sunday. This market is ideal for sampling delicious treats and enjoying the lively atmosphere.
Riverwalk
The Chicago Riverwalk is a scenic attraction perfect for a stroll. Enjoy watching the boats on the Chicago River and exploring the various public art installations. One of the best things about the riverwalk is that you can stop at one of the many cafes for a snack break.
Ride Bikes or Walk on the Lakefront Trail
The Lakefront Trail offers stunning views of Lake Michigan and is a great way to stay active. Rent bikes or walk along the trail, suitable for all ages with plenty of spots to stop and rest or have a picnic.
Ride Bikes or Walk on the 606
The 606 is an elevated trail that spans several neighborhoods, excellent for biking or walking. It’s lined with parks and art installations, making it an engaging experience.
Visit Montrose Beach
If you've never seen the shores of Lake Michigan, you absolutely need to visit its sandy beaches! Montrose Beach is the best beach for families - it's spacious with plenty of room for kids of all ages to run, play, and swim. Ohio Street Beach is another excellent option if you’re closer to downtown. Bring beach toys, sunscreen, and plenty of water for a fun day in the sun.
Visit Buckingham Fountain
Located in Grant Park, Buckingham Fountain is one of Chicago’s most iconic landmarks. It’s a great spot for a picnic and to let the kids burn off some energy. Visit in the evening to see the fountain’s light show for an extra special experience.
Chicago Botanic Garden
The Chicago Botanic Garden is a beautiful retreat for nature lovers, located a short distance from downtown Chicago. Open daily, it spans over 385 acres and features 27 distinct gardens, including the enchanting Japanese Gardens. It's the perfect place to immerse yourself in natural beauty and enjoy the changing seasons. Whether you're taking a leisurely stroll, participating in a gardening workshop, or attending one of their seasonal events, there's always something new to discover.
Take a Walking Tour
Taking a walking tour of Chicago is an awesome way to dive into the city's rich history, stunning architecture, and vibrant culture. With a knowledgeable tour guide leading the way, you can explore iconic spots like Millennium Park, the Chicago Riverwalk, and historic neighborhoods like Wicker Park and Oak Park. These tours give you a unique glimpse into Chicago's past and present, showcasing its transformation into one of the most dynamic cities in the United States.
Catch a Movie in the Park
Enjoying a movie in the park is a classic Chicago summer activit. Grant Park and Millennium Park host free outdoor movie screenings throughout the warmer months. Bring a blanket, snacks, and enjoy a film under the stars. It’s the perfect way to unwind after a busy day exploring the city. Check the Chicago Park District’s website for dates and times.
Shop on Michigan Ave
Michigan Avenue, aka the Magnificent Mile, is a shopper's paradise. Don’t miss the massive Starbucks Reserve Roastery for a unique coffee experience. For a luxurious treat, have lunch or coffee at RL Restaurant by Ralph Lauren, known for its delicious food and elegant setting. This area is perfect for experiencing some of the best shopping in Chicago.
Local Shopping
For a more local vibe, check out Southport Corridor at Southport and Addison. This area is full of charming boutiques and big-name stores. For even more shopping, head to Six Corners at Milwaukee, Damen, and North Avenue. While you're there, don’t miss Big Star for some mouthwatering tacos and a refreshing margarita. These spots offer a mix of local flavor and trendy shopping.
Head to Fulton Market for Lunch or Dinner
Fulton Market is a foodie’s dream. Whether you're in the mood for casual bites or upscale dining, you’ll find it here. Favorites include Beatrix, The Allis at Soho House, Rosemary, and Saigon Sisters. Each spot offers something unique, making Fulton Market a must-visit for any food lover.
Indoor Things to Do in Chicago
Go to the Top of Willis Tower
Visiting the Willis Tower, once known as the Sears Tower, is a must on any list of Chicago day trip ideas. As the tallest building in Chicago, it offers breathtaking views of the city skyline and beyond. The best time to visit is early morning or late afternoon to avoid the largest crowds and enjoy the stunning light of sunrise or sunset.
The Skydeck, located just a short distance from downtown Chicago, features The Ledge, a glass box extending out from the tower, giving you the thrilling experience of standing 1,353 feet above the city streets.
Shedd Aquarium
The Shedd Aquarium offers a mesmerizing glimpse into the underwater world. From the giant beluga whales to the playful sea otters, there's something here for everyone. Don’t miss the free admission days by looking them up in advance.
Chicago Architecture Center
The Chicago Architecture Center is a must-visit for those interested in the city's iconic buildings and rich architectural history. Located on the banks of the Chicago River, it's the starting point for the popular architecture river cruise, which provides stunning views and fascinating insights into Chicago's historic sites.
Museum of Science & Industry
The Museum of Science & Industry features tons of interactive exhibits and hands-on learning. Highlights include the U-505 submarine and the giant Tesla coil. Plan to spend a whole day here exploring all the exhibits.
Chicago History Museum
For a deep dive into the rich history of the Windy City, the Chicago History Museum is a must-visit. Exhibits cover everything from the Great Chicago Fire to the city’s role in the Civil Rights Movement.
Field Museum
Home to the world-famous dinosaur, Sue, the Field Museum is one of the top places for those fascinated by natural history. Plan to spend a few hours exploring the vast collection of artifacts and exhibits.
Peggy Notebaert Nature Museum
The Peggy Notebaert Nature Museum is particularly great for nature lovers. The butterfly haven is a highlight, where you can walk among hundreds of live butterflies.
Garfield Park Conservatory
The Garfield Park Conservatory is a lush, indoor oasis perfect for exploring different plant species and exhibits. It’s educational and offers free admission.
Lincoln Park Conservatory
Similar to Garfield Park, the Lincoln Park Conservatory offers a tranquil indoor escape filled with beautiful plants and flowers. It's the best way to cool off during the summer months!
Navy Pier
Navy Pier is a Chicago landmark that offers endless fun. From the Chicago Children's Museum to the IMAX theater, there's something for everyone.
Best Places to Eat in Chicago
Whether you're a local or a visitor, Chicago's food scene has something to offer everyone. From brunch spots to steakhouses, here's a guide to some of the best places to eat in Chicago, categorized for your convenience.
Best Brunch Spot: The Bongo Room
Located in the heart of the South Loop, The Bongo Room is a favorite brunch spot known for its creative and decadent dishes. Their stuffed French toast and seasonal pancakes are a must-try. The laid-back atmosphere makes it perfect for a leisurely weekend brunch.
Best Place to Eat with Kids: Portillo’s
Portillo’s is a Chicago staple, perfect for a family-friendly meal. Known for its Italian beef sandwiches, Chicago-style hot dogs, and chocolate cake shakes, it's a hit with both kids and adults. The fun, retro decor adds to the appeal, making it an enjoyable dining experience for the whole family.
Best Steakhouse: Gibsons Bar & Steakhouse
Gibsons is a Chicago icon, offering some of the best steaks in the city. Located in the Gold Coast neighborhood, this steakhouse is renowned for its USDA Prime steaks, fresh seafood, and classic cocktails. The lively atmosphere and impeccable service make it a top choice for a special night out.
Best Happy Hour: Three Dots and a Dash
For a fun and unique happy hour experience, head to Three Dots and a Dash, a hidden tiki bar in River North. Known for its tropical cocktails and Polynesian-inspired bites, this bar offers a vibrant, island-like escape in the middle of the city. Their happy hour specials on drinks and appetizers are not to be missed.
Best Rooftop: Cindy’s Rooftop
Located atop the Chicago Athletic Association Hotel, Cindy’s Rooftop offers stunning views of Millennium Park and Lake Michigan. The menu features seasonal, shareable plates and inventive cocktails. It’s the perfect spot for a sunset drink or a weekend brunch with a view.
Best Pizza: Lou Malnati’s Pizzeria
No visit to Chicago is complete without trying its famous deep-dish pizza, and Lou Malnati’s is one of the best places to do just that. With locations all over the city, this pizzeria is known for its buttery crust, rich tomato sauce, and generous toppings. The “Lou” pizza, with spinach, mushrooms, and sliced tomatoes, is a local favorite.
Best Food Hall: Time Out Market Chicago
Located in the Fulton Market District, Time Out Market brings together some of the best chefs and eateries in the city under one roof. From BBQ to sushi, the variety of food options ensures that there’s something for everyone. The market also features a rooftop bar, offering great views and a fun atmosphere.
Best Vegan: The Chicago Diner
Since 1983, The Chicago Diner has been serving up delicious vegan and vegetarian fare. Their signature Radical Reuben, made with seitan, is a must-try. With locations in Logan Square and Lakeview, this diner is a go-to for plant-based comfort food.
Best Seafood: Shaw’s Crab House
For seafood lovers, Shaw’s Crab House is a must-visit. Located in River North, Shaw’s offers a variety of fresh seafood dishes, including their famous Alaskan King Crab and oysters. The vintage decor and classic vibe make it a great spot for a date night or special occasion.
Best Fine Dining: Alinea
Alinea is more than just a meal; it’s an experience. This three-Michelin-star restaurant in Lincoln Park is known for its innovative and artistic approach to cuisine. Chef Grant Achatz’s tasting menus are constantly evolving, offering diners a truly unique and unforgettable experience. Reservations are a must, and the price tag reflects the level of creativity and precision in each dish.
Best Casual Dining: Parson’s Chicken & Fish
For a laid-back dining experience with great food, head to Parson’s Chicken & Fish in Logan Square. Known for its fried chicken, fish sandwiches, and frozen cocktails, Parson’s is the perfect spot for a casual meal with friends. The outdoor patio, complete with a ping-pong table and fire pit, adds to the relaxed vibe.
Best Bakery: Mindy’s Bakery
Mindy Segal’s bakery in Bucktown is a haven for sweet tooths. Known for her creative takes on classic baked goods, Mindy’s Bakery offers a variety of pastries, cookies, and breads. The chocolate chip cookies and hot chocolate are particularly popular.
Best Hot Dog: Superdawg Drive-In
An iconic Chicago institution, Superdawg Drive-In has been serving up its unique take on the Chicago-style hot dog since 1948. The Superdawg comes with all the classic toppings and is served in a vintage drive-in setting, making it a fun and nostalgic dining experience.
Best Ethnic Cuisine: Girl & the Goat
Owned by renowned chef Stephanie Izard, Girl & the Goat in the West Loop offers a globally inspired menu with dishes influenced by Asian, Mediterranean, and Latin American cuisines. The atmosphere is lively, and the food is innovative and delicious. The roasted cauliflower and goat empanadas are standout dishes.
Best Ice Cream: Jeni’s Splendid Ice Creams
Jeni’s Splendid Ice Creams, with locations in Wicker Park and Lincoln Park, is a must-visit for ice cream lovers. Known for its high-quality ingredients and creative flavors, Jeni’s offers something for everyone. Popular flavors include Brambleberry Crisp and Salty Caramel.
Best for a Romantic Dinner: Geja’s Cafe
For a truly romantic dining experience, head to Geja’s Cafe in Lincoln Park. This fondue restaurant offers a cozy, intimate atmosphere perfect for a date night. The combination of cheese fondue, meat and seafood cooked at the table, and chocolate fondue for dessert makes for a memorable meal.
Chicago’s dining scene is as diverse as the city itself, offering everything from high-end dining experiences to casual eateries and everything in between. Whether you’re looking for a spot for brunch, a family-friendly restaurant, or a romantic dinner, Chicago has it all.
Best Day Trips from Chicago
If you're spending some time in the city and want to explore what the surrounding area has to offer, consider one of these day trip ideas from Chicago.
Lake Geneva
Just a short drive from Chicago, Lake Geneva in Wisconsin is a charming resort town known for its beautiful lake and scenic surroundings. Enjoy a relaxing day on the water with various water sports, or take a stroll along the lakefront. The town also offers unique shops and delightful coffee shops to explore.
Indiana Dunes National Park
For nature lovers, Indiana Dunes National Park is a must-visit. Located along the southern shore of Lake Michigan, it boasts stunning sand dunes, diverse ecosystems, and plenty of opportunities for hiking and bird watching. It’s one of the best weekend getaways for those seeking a mix of adventure and tranquility.
Oak Park
Home to the world’s largest collection of Frank Lloyd Wright buildings, Oak Park is perfect for architecture enthusiasts. This historic neighborhood offers a chance to explore national historic landmarks and take guided walking tours of Wright’s major works. Don’t miss visiting the home and studio of Frank Lloyd Wright, a true architectural gem.
Six Flags Great America
For thrill-seekers, Six Flags Great America in Gurnee is a fantastic choice. This theme park features an array of roller coasters and attractions for all ages. Additionally, it has a water park where you can cool off during the summer months. It’s an ideal destination for a fun-filled family adventure.
Starved Rock State Park
Starved Rock State Park along the Illinois River is renowned for its stunning canyons, waterfalls, and hiking trails. It’s a great spot for a family road trip, offering activities like boating, fishing, and picnicking. The park's natural beauty makes it a favorite among nature enthusiasts and photographers.
Michigan City
Michigan City, located along the shores of Lake Michigan, offers a blend of small-town charm and lakeside recreation. Visit the sandy beaches, explore the local shops, or take a train ride to the nearby Indiana Dunes National Park. It’s an excellent spot for a relaxing day by the water.
South Bend
Home to the University of Notre Dame, South Bend is rich in history and culture. Take a tour of the university’s beautiful campus, visit the South Bend Chocolate Factory, or explore the city’s museums and parks. It’s a great place for a day trip filled with learning and exploration.
Milwaukee Art Museum
A trip to Milwaukee wouldn’t be complete without visiting the Milwaukee Art Museum. Known for its striking architecture and floor-to-ceiling windows, the museum houses a vast collection of major works of art. Combine your visit with a stroll along the lakefront for a perfect cultural day trip.
These destinations, all within a short distance from Chicago, provide a diverse range of activities and sights, making them the best places for memorable day trips.
Planning Your Day Trip
When planning your Chicago day trip, consider these tips to make the most of your adventure:
Start Early: To maximize your time and experience all the Windy City has to offer, kick off your day trip bright and early. Not only will you beat the crowds at popular attractions, but you’ll also have more time to explore the hidden gems of the city.
Public Transportation: Chicago's public transportation system, including the CTA buses and "L" trains, is an efficient and cost-effective way to navigate the city. You can easily hop on and off to visit various attractions without the hassle of finding parking. Consider getting a day pass for unlimited rides, which can save you time and money.
Comfortable Shoes: Chicago is a city best experienced on foot. With its array of attractions, parks, and architectural wonders, you'll be doing a lot of walking. Make sure to wear comfortable shoes to keep your feet happy and avoid fatigue as you explore neighborhoods like the Magnificent Mile, Millennium Park, and beyond.
Weather: Chicago weather can be quite unpredictable, with rapid changes from sunshine to rain. Check the weather forecast before you head out and dress in layers. This way, you can adjust to the changing temperatures and stay comfortable throughout your day. Don’t forget essentials like sunglasses, an umbrella, or a hat, depending on the forecast.
Plan Your Route: Map out your key destinations in advance and plan an efficient route to minimize travel time. Prioritize the must-see attractions, but leave some room for spontaneous stops at coffee shops, parks, or unique boutiques that catch your eye.
Hydrate and Snack: Walking and exploring can be tiring, so keep hydrated and pack some snacks. Chicago has numerous food options, but having water and a quick snack handy can keep your energy up between meals.
Cultural Experiences: Incorporate a mix of activities into your day. Visit a museum in the morning, enjoy lunch at a local eatery, take an afternoon architecture river cruise, and finish with a sunset at one of the city’s rooftop bars. This variety will give you a well-rounded taste of Chicago’s rich culture and history.
By following these tips, you’ll ensure a smooth and enjoyable day trip in Chicago, packed with memorable experiences and new discoveries.
Come Explore Chicago!
Chicago is a city that offers endless opportunities for exploration and fun. Whether you're planning a family outing or a day trip with friends, there's something for everyone. From iconic landmarks and museums to vibrant neighborhoods and culinary delights, Chicago promises a memorable experience for all. So pack your bags, grab your camera, and get ready to discover the best of Chicago!
Have questions about spending a day in Chicago? I'd love to help answer!
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Hi, I’m Jen!
Hi, I’m Jen, your perpetually optimistic, fun-loving, witty friend. When I’m not working at The Marketing Greenhouse, you can find me gardening in the sun, playing games with my kids or creating content that inspires people to try new things and be the best version of themselves.
