Best Things to Do in Chicago (From Someone Who Fell in Love With It)

Chicago isn’t just another big city it’s a place with heart. Set along Lake Michigan, it blends skyscrapers with sandy beaches, deep-rooted culture with ever-evolving neighborhoods. I came here expecting great pizza and pretty views. I left with a camera roll full of public art, a new appreciation for jazz, and the kind of memories that make you want to come back.

A Quick Look at Chicago’s History

Founded in 1833, Chicago quickly rose from a small trading post to one of America’s most dynamic cities. It rebuilt itself after the Great Fire of 1871 and became a pioneer in architecture and industry. Known for its jazz and blues scenes, deep-dish pizza, and contributions to literature and politics, Chicago has always been a city of reinvention. Today, it’s a vibrant cultural hub that honors its past while staying fiercely modern.

Where to Stay in Chicago

Whether you’re looking for luxury, charm, or budget options, Chicago has a neighborhood for every kind of traveler:

• The Loop – Ideal for first-time visitors, with easy access to top attractions.
• River North – Great for nightlife, galleries, and boutique hotels.
• West Loop – A foodie’s paradise with trendy, upscale hotels.
• Lincoln Park – Family-friendly with a residential feel and nature.
• Budget tip: Check out HI Chicago Hostel or Freehand Chicago for affordable stays without compromising on location.

Recommended Hotels in Chicago (Affiliate Picks)

Here are a few places I personally recommend for every budget. All are well-rated, centrally located, and offer easy access to transit and top attractions:

• citizenM Chicago Downtown ($) – Modern, tech-savvy, and great for solo travelers or digital nomads. Small but super functional rooms right in the Loop.
• Sofitel Chicago Magnificent Mile ($$) – Sleek and stylish with French-inspired luxury, steps from upscale shopping and dining.
• Thompson Chicago ($$$) – A boutique experience with artful interiors and a prime location in the Gold Coast. Great for couples.
• Viceroy Chicago ($$$) – Chic and photogenic with rooftop views, perfect for trendy travelers or a romantic getaway.
• The Langham, Chicago ($$$$) – Ultimate luxury with river views, top-tier service, and a tranquil spa, worth the splurge.

Note: Some of the links above may be affiliate links, which means I may earn a small commission (at no extra cost to you) if you decide to book through them. I only recommend places I’d stay myself!

What to Pack for Chicago (By Season)

Chicago weather is famously unpredictable, so packing smart makes a difference:

• Spring (March–May): Layers, umbrella, sneakers, light jacket.
• Summer (June–August): Sunscreen, sunglasses, water bottle, casual summer wear.
• Fall (September–November): Windbreaker, closed shoes, scarf, raincoat.
• Winter (December–February): Heavy coat, thermal layers, gloves, hat, waterproof boots.

Top Tours and Experiences in Chicago

Hidden Gems I Loved in Chicago

Looking to go beyond the tourist trail? These under-the-radar places truly made my Chicago trip feel personal and memorable:

• The 606 Trail – Once a rail line known as the Bloomingdale Line, the 606 Trail has been transformed into an elevated, 2.7-mile-long pedestrian and cycling path that links several northwest neighborhoods, including Wicker Park, Bucktown, and Logan Square. I rented a Divvy bike and cruised past vibrant murals, blooming community gardens, and outdoor sculptures. There are multiple access points and plenty of shaded benches for relaxing. It’s also a popular route for morning joggers and neighborhood strolls. Don’t miss the lookout points for unexpected views of the city skyline.

• Garfield Park Conservatory – Often called “landscape art under glass,” this massive greenhouse is one of the largest and most stunning conservatories in the country. With eight indoor garden rooms and 10 acres of outdoor gardens, it’s a floral wonderland year-round. The Palm House took my breath away, it felt like I’d been transported to the tropics. Seasonal flower shows, educational exhibits, and art installations add extra magic. It’s a favorite escape in winter, but gorgeous in every season. Bonus: it’s easy to reach via the CTA Green Line (just hop off at Conservatory-Central Park Drive).

• Promontory Point – Located in Burnham Park, this lakeside spot was quiet even on a sunny weekend. Locals come here to picnic, swim, or just enjoy uninterrupted views of the downtown skyline. I brought my coffee and journal here one morning and stayed for hours.

• The Charnel House – Tucked away in Logan Square, this repurposed funeral home now hosts intimate and experimental theatre performances. It’s raw, authentic, and creatively alive. If you’re into indie arts, check their schedule you might stumble on something unforgettable.
• The Magic Parlour – A classy, interactive magic show inside a historic hotel downtown. It’s one of those unique Chicago experiences you won’t find in guidebooks, and I still can’t figure out how the magician pulled off his final trick.
• Osaka Garden in Jackson Park – This serene Japanese garden feels like a hidden world, especially during cherry blossom season. It’s a short walk from the Museum of Science and Industry but rarely crowded. I loved the peaceful bridges and quiet landscaping.

If you’ve already seen the big sights, these hidden gems will show you a softer, more local side of Chicago that’s full of personality.

Easy Day Trips from Chicago

Travel Time Tip: You can reach these destinations using a combination of Metra trains, CTA, or regional lines. Here’s how long it generally takes to get to each one:

• Oak Park – 25 mins from the Loop via CTA Green Line or Metra UP-West Line
• Evanston – 30–40 mins via CTA Purple Line or Metra UP-North Line
• Indiana Dunes National Park – 70–90 mins via South Shore Line from Millennium Station or by car

These day trips are convenient and accessible, perfect if you want a quick escape while staying based in the city.
If you’re staying in Chicago for more than a long weekend, these day trips offer a refreshing change of pace and a deeper look at the region’s diversity:

• Oak Park – Just a 25-minute train ride from downtown, Oak Park is a must for architecture lovers. It’s home to the Frank Lloyd Wright Home and Studio, where the legendary architect developed his signature Prairie style. You can also take a walking tour to see dozens of Wright-designed homes in the neighborhood. The town itself has a cozy, historic feel with cafes and indie bookshops.

• Evanston – Head north along the Purple Line to this picturesque college town that’s home to Northwestern University. Evanston’s walkable downtown is filled with boutiques, bakeries, and lakefront parks. On a warm day, Clark Street Beach is perfect for a swim or a picnic. It’s one of my favorite spots to escape the city without really leaving it.

• Indiana Dunes National Park – About an hour from the city by car or South Shore Line train, Indiana Dunes is a nature lover’s dream. Hike through sandy dunes, climb wooded trails, or relax on quiet beaches along Lake Michigan. It’s peaceful, scenic, and surprisingly wild especially beautiful during early fall when the leaves start turning.

Each of these trips offers a different slice of life around Chicago, whether you’re into architecture, college town charm, or untouched nature. If you have the time, they’re absolutely worth the detour.

Top Tips for First-Time Visitors

Here are a few things I wish I knew before my trip:

• Avoid driving downtown parking is expensive and traffic can be tricky.
• Most museums have free or discounted days (check ahead!).
• Always tip at restaurants and bars (15–20%).
• Book popular attractions like Skydeck or cruises in advance during summer.
• Be ready for the weather to change Chicago is known for surprises!

My 3-Day Chicago Itinerary (At a Glance)

Day 1: Architecture cruise, Riverwalk, Millennium Park, Cloud Gate (“The Bean”), Art Institute
Day 2: Museum Campus (Shedd Aquarium or Field Museum), Lakefront Trail, Navy Pier, jazz club
Day 3: Wicker Park + Pilsen neighborhoods, deep-dish pizza, Lincoln Park Zoo or rooftop bar

Explore Chicago’s Iconic Attractions

Take an Architecture River Cruise

This was hands-down my favorite experience in the city. Chicago is often referred to as the birthplace of the skyscraper, and the best way to appreciate its architectural legacy is from the water. The architecture cruise floats along all three branches of the Chicago River while guides share captivating stories about the rise of the city from the Great Chicago Fire to modern feats of engineering. Highlights include the Wrigley Building, Marina City (aka the “corn cobs”), and Aqua Tower.

If there’s one tour I always recommend, it’s the Chicago Architecture River Cruise on Viator. It’s consistently top-rated for a reason – amazing views, fascinating stories, and a totally unique way to experience the city. It’s the most popular way to see the city’s skyline from the water – and it sells out fast!

Tip: Book the Chicago Architecture Foundation Center tour for the most informative experience. Golden hour or twilight cruises offer magical lighting for photography.

Stroll the Chicago Riverwalk

After the cruise, I wandered the Riverwalk, which stretches from Lake Shore Drive to Lake Street. This beautifully landscaped promenade is lined with cafes, beer gardens, museums, art installations, and even kayaking docks. I stopped for coffee at Tiny Tapp and watched the boats drift by. If you’re looking to rest your feet, this is a dreamy spot to take a breather and snap a few lakeside skyline shots.

Pro Tip: The Riverwalk is divided into distinct sections like The Marina, The Cove, and The Jetty each with its own vibe and features.

Visit Millennium Park and Cloud Gate

Millennium Park is far more than a photo-op with Cloud Gate. It’s an artistic and cultural space that locals truly use. I saw kids playing at Crown Fountain, heard a live jazz quartet by Pritzker Pavilion, and admired massive public sculptures scattered across the lawn. There’s a peaceful garden walk, seasonal exhibitions, and even a skating rink in the winter.

Don’t Miss: Lurie Garden in spring and the summer music series for a local experience.

Go Sky-High: Skydeck vs. 360 CHICAGO

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For unbeatable panoramic views of Chicago’s city grid and Lake Michigan, head up literally. The Skydeck at Willis Tower (formerly Sears Tower) has the famous glass ledge extending four feet outside the building’s 103rd floor. The 360 CHICAGO Observation Deck in the John Hancock building offers Tilt, a platform that angles you outward from the 94th floor for a thrilling (but secure!) view.

• Skydeck: Great for brag-worthy photos and central city views.
• 360 CHICAGO: Less crowded and better views of the lake and northern neighborhoods.

Book ahead for sunset slots both decks offer dazzling views at golden hour followed by city lights at dusk.

Get to Know the Neighborhoods

Travel Time Tip: Most neighborhoods listed below are accessible via CTA trains or buses from the Loop. Here’s how long it generally takes to reach each area:

• West Loop – 10 mins by bus or 20 mins walking from the Loop
• Wicker Park – ~15–20 mins on the Blue Line
• Lincoln Park – ~20 mins via Red or Brown Line
• Pilsen – ~15 mins via Pink Line or by Uber from the Loop

Use a Ventra card for quick, tap-in access to CTA trains and buses. Most train lines run every 5–10 minutes during the day.

The Loop

The Loop is Chicago’s bustling downtown core and the heartbeat of the city. It’s home to iconic sights like Millennium Park, The Art Institute of Chicago, and Willis Tower. You’ll also find the Chicago Theatre, State Street shopping, and architectural landmarks along almost every block. This is the best area for first-time visitors who want to stay close to top attractions and have easy access to public transportation. During weekdays, the Loop buzzes with professionals; on weekends, it’s more laid-back.

West Loop

Once an industrial warehouse district, the West Loop is now Chicago’s trendiest culinary neighborhood. Its transformation has turned it into a hotspot filled with Michelin-starred restaurants, hip cocktail bars, and stylish boutiques. Head to Randolph Street (a.k.a. Restaurant Row) for everything from upscale dining at Girl & the Goat to creative fusion tacos and Korean BBQ. The area also has cool art galleries and loft-style hotels, making it perfect for foodies and design lovers.

Wicker Park

Wicker Park blends artistic grit with modern cool. It’s known for its vintage stores, indie bookstores like Volumes, art murals, and third-wave coffee shops. I spent a morning thrifting on Milwaukee Avenue and sipping coffee at Ipsento. There’s always something happening farmers markets, pop-up galleries, live music. It’s ideal for travelers who want to experience Chicago’s creative, youth-driven culture.

Lincoln Park

Leafy, residential, and family-friendly, Lincoln Park is a breath of fresh air. It’s home to the Lincoln Park Zoo (which is free), the peaceful Lincoln Park Conservatory, and stunning lakefront views. I loved walking the Nature Boardwalk, spotting birds and turtles right in the city. You’ll also find historic brownstones, DePaul University’s campus, and casual brunch spots all over. This neighborhood is great for travelers who want a quieter, green escape without leaving the city.

Pilsen

Pilsen is one of Chicago’s most culturally rich and visually inspiring neighborhoods. Known for its strong Mexican-American heritage, you’ll find vibrant street murals, traditional bakeries, taquerias, and the phenomenal National Museum of Mexican Art. The community vibe here is real walk down 18th Street and you’ll see public art, colorful storefronts, and hear Spanish spoken all around. I recommend coming hungry and curious there’s no better way to explore Pilsen than with a camera and an appetite.

Chicago for Art, Music & Museum Lovers

Wander the Art Institute of Chicago

This world-renowned museum is a must for art lovers. I spent hours exploring the Impressionist wing, where Monet’s water lilies and Van Gogh’s self-portraits hang in peaceful galleries. Don’t miss the Thorne Miniature Rooms tiny, detailed replicas of historic interiors that are surprisingly mesmerizing. If you’re into American art, you’ll find Grant Wood’s American Gothic here too.

Insider Tip: Entry is free for Illinois residents on Thursday evenings. Arrive early to avoid crowds and enjoy quieter galleries.

Dive into Museum Campus

Located along the lakefront just south of downtown, Museum Campus is home to three major institutions:

• The Shedd Aquarium: Explore over 30,000 aquatic animals, including beluga whales, penguins, and reef sharks. It’s especially fun for kids.
• The Field Museum: Home to Sue, the largest and most complete T. rex fossil ever found. There’s also an Ancient Egypt exhibit, and rotating exhibitions on natural history.
• The Adler Planetarium: The oldest planetarium in the Western Hemisphere, with immersive space exhibits, shows, and unbeatable skyline views from its steps.

Travel Tip: You can easily walk between all three museums and relax by the water in between. Bundle admission with a CityPASS for savings.

Discover Chicago’s Public Art

Chicago is like one giant outdoor gallery. In addition to Cloud Gate (The Bean), keep your eyes open for:

• Crown Fountain – One of the most unique public art installations in the city, Crown Fountain features two 50-foot glass brick towers facing each other across a shallow reflecting pool. The towers display digital video portraits of everyday Chicagoans, and during warm months, they periodically spout water from the mouths of the faces, much to the delight of children and families splashing below. It’s playful, unexpected, and interactive in a way that few public art pieces are. I visited in the summer and loved watching kids giggle as they waited for the next surprise splash. The installation is especially photogenic at twilight when the LED-lit faces glow against the city skyline.

• The Flamingo by Alexander Calder – A bold red sculpture set against modernist buildings in the Federal Plaza.
• Four Seasons Mosaic by Marc Chagall – Tucked near the Chase Tower, this dreamlike piece deserves a stop.
• Murals in Logan Square and Pilsen – I loved wandering 16th Street in Pilsen for its block-long stretches of vibrant, expressive art.

Pro Tip: Download the Chicago Public Art app to track and learn about over 500 outdoor pieces throughout the city.

Catch Live Jazz or Blues at Night

Chicago’s music scene is legendary and still alive today. My favorite experience was stepping into Green Mill Cocktail Lounge, a moody Uptown bar that oozes Prohibition-era charm. Legend has it Al Capone had his own booth there. The cocktails were strong, and the jazz trio? Flawless.

Other great spots:

• Buddy Guy’s Legends – Chicago blues at its finest, with a rotating list of big names and surprise performances.
• Andy’s Jazz Club – More upscale with dinner service and a polished atmosphere.
• Kingston Mines – Two stages, late hours, and a down-to-earth crowd. If you love live music, stay late you won’t regret it.

Travel Tip: Some clubs offer early sets or weekday discounts. Arrive early for seating, especially on weekends.

Where to Eat (Beyond Deep Dish)

Deep Dish Pizza Showdown

No trip to Chicago is complete without trying deep-dish pizza, and I made it a mission to compare the best.

• Lou Malnati’s: Their signature buttery, cornmeal crust stands out. It’s flaky yet sturdy enough to hold the layers of gooey cheese and rich tomato sauce.
• Giordano’s: This is the go-to for traditional stuffed deep dish. Expect a thick crust with ample cheese and sauce packed into every bite. Great for sharing.
• Pequod’s: A cult favorite known for its caramelized cheese crust that clings to the edge of the pan. The vibe here is more casual and local, which I loved.

Tip: Deep dish takes around 45 minutes to bake, so call ahead or snack before you arrive.

Must-Try Local Eats

Chicago’s food scene goes far beyond pizza. Here are a few other signature bites and beloved spots that stood out:

• Italian Beef Sandwich at Portillo’s: Thinly sliced, seasoned beef stuffed into a soft roll, dipped in savory jus. Order it “dipped” and topped with spicy giardiniera if you’re feeling brave. It’s messy but worth it.
• Chicago-Style Hot Dog: A true Chicago dog is an all-beef frank on a poppy seed bun, topped with yellow mustard, neon green relish, onions, tomato wedges, a pickle spear, sport peppers, and a dash of celery salt absolutely no ketchup. Get yours from Gene & Jude’s or Superdawg Drive-In for authenticity.

• Au Cheval: Their double cheeseburger is legendary perfectly seared patties, melty cheese, dijonnaise, and a soft bun. It’s often voted the best burger in the U.S., and I can see why.
• Time Out Market: If you’re with a group or unsure what you’re craving, this curated food hall in the West Loop has options from top Chicago chefs. Try fried chicken from Pretty Cool Ice Cream or bao from Chef Bill Kim.
• Girl & the Goat: This award-winning restaurant by Stephanie Izard is a modern American dining experience with bold, globally inspired flavors. I ordered the goat empanadas and roasted cauliflower and would go back in a heartbeat.

Bonus Pick: Try Jibaritos (plantain sandwiches) in Humboldt Park or grab a donut from Do-Rite Donuts if you have a sweet tooth.

Chicago is a paradise for food lovers come hungry, and don’t be afraid to venture outside the tourist zones to try what the locals swear by.

Seasonal Tips & Events

Chicago in Summer

• Lollapalooza in Grant Park (July)
• Taste of Chicago (July)
• Chicago Blues Festival (June)
• Rooftop bars like Cindy’s or LondonHouse
• Kayaking on the Chicago River

Chicago in Winter

• Christkindlmarket (November–December)
• Ice skating at Maggie Daley Park
• Indoor fun at museums and jazz clubs

Relax at the Beach

Yes, Chicago has beaches! Thanks to its Lake Michigan shoreline, summer in the city means sunbathing, volleyball, and skyline views without ever leaving town.

• North Avenue Beach: This is Chicago’s most popular beach, especially among younger crowds and groups. It has a party vibe on weekends, with a lively mix of sunbathers, beach bars like Castaways, and rental options for paddleboards and bikes. I found it perfect for people-watching and grabbing a frozen drink with a view.

• Oak Street Beach: Just north of the Magnificent Mile, this beach feels more relaxed and upscale. The sand is soft, the water is calm, and the views of the skyline are spectacular especially at sunset. It’s great for solo travelers, couples, or anyone looking for a chill lakeside afternoon.

• Montrose Beach: Located in Uptown, this is one of the largest beaches in the city. There’s space to spread out, a dog-friendly area, and even a bird sanctuary nearby. It’s ideal if you want fewer crowds or are visiting with a pet.

Tip: Bring your own towel, water, and sunscreen. Beach access is free, but amenities vary by location. Early mornings and weekdays are best for quieter experiences.

Getting Around Chicago

Chicago is a city made for walking but when your feet need a break, there are plenty of efficient ways to get around:

• L Train (CTA): The elevated train system (locals just call it the “L”) is fast, affordable, and connects nearly all major neighborhoods and attractions. Use the Red, Blue, Brown, Pink, and Green Lines for most tourist stops. Trains run frequently and are reliable even late at night.
• CTA Passes: I recommend getting a Ventra Card or a 1-Day or 3-Day CTA pass if you’re planning to use public transit a lot. You can tap in at any station or bus stop.
• Divvy Bikes: Chicago’s bike-share system is a fun way to explore neighborhoods and the Lakefront Trail. The bikes are docked all around the city and are easy to rent via app.

• Rideshare: Uber and Lyft are widely available. Use them late at night or when traveling to/from outer neighborhoods like Hyde Park or airport transfers.
• Water Taxi: In warmer months, hop on a water taxi between downtown stops like Navy Pier, the Riverwalk, and Chinatown. It’s cheap, scenic, and much less stressful than city traffic.

Pro Tip: Google Maps integrates with CTA and Divvy bike locations. Use it to plan real-time routes and save time.

FAQs About Visiting Chicago

If you’re planning a trip to Chicago and want even more inspiration, check out my upcoming guides to the best hotels and weekend itineraries. Until then, happy travels!