At Bobby’s Bike Hike & Food Tours, we’re often asked the same question: “What are the best things to do in Chicago?” After leading thousands of guests through the city by bike and on foot, we’ve learned the answer isn’t just a list—it’s a route. Many of Chicago’s must-see sights, from the river to the lakefront, naturally fall along our tour paths, which means we experience (and refine) these highlights every single day.
Chicago is a big city with a big personality—equal parts skyline and lake breeze. Downtown hums with energy, yet walk a couple blocks and Lake Michigan reminds you you’re still anchored by water and parks. Unlike New York, Chicago pairs big-city scale with Midwestern ease. As Anthony Bourdain said, “You wake up in Chicago, pull back the curtain and you know where you are. You could be nowhere else.”
In this first‑timer guide, we’ll share the best things to do downtown, along the water, above the skyline, and inside the neighborhoods that give the city its character, and show you which ones you can check off your list on a Bobby’s Bike Hike tour.
Downtown Favorites: Where Everyone Starts
– Millennium Park and The Bean (Cloud Gate)
Millennium Park is Chicago’s “you’ve arrived” moment. Walk beneath the silver ribbons of architect Frank Gehry’s Pritzker Pavilion, then drift to Cloud Gate—better known as The Bean—for that essential mirror-polished selfie. Cross Gehry’s snaking BP Bridge to the gardens and you’ll land steps from the lakefront trails that trace Lake Michigan. In summer, free things like concerts and festivals keep the lawn humming; in winter, the ribbon ice path curls through the park under the skyline.
– Art Institute of Chicago
One of the world’s great museums sits right next door. The Art Institute of Chicago balances “must-see” icons (hello, Monet and Seurat) with contemporary works in the Modern Wing. First timers can comfortably see highlights in two hours, especially if you plan a simple loop. If you’re stacking multiple attractions, consider CityPASS to streamline admission across several stops.
– Chicago Cultural Center
A short walk north brings you to the Chicago Cultural Center, a free temple to the arts with murals, mosaics, and the famous Tiffany glass dome. Rotating exhibits and performing arts programs make it an easy add between Millennium Park and The Loop’s theaters.
(Want to see the best of downtown without missing a highlight? Chicago Highlights & Attractions Walking Tour and our Chicago Favorites Food & Walking Tour hit most of these spots—with storytelling and snacks along the way.)
Michigan Avenue Magic
– The Chicago River (DuSable Bridge)
At Michigan Avenue and the Chicago River you can frame classic skyline shots and easily step down to either bank for a waterside view. This is also where some of the famous Chicago Architecture Boat Cruises start from.
– Walk the Magnificent Mile
From the Chicago River to Oak Street, the Magnificent Mile blends historic architecture, modern skyscrapers, and nonstop people-watching. Along the way, browse big names like Nike and Uniqlo, stop at the Starbucks Reserve Roastery (the largest Starbucks in the world) or pop into immersive attractions such as the Museum of Ice Cream or seasonal themed pop-ups. Whether you’re shopping, sipping, or just taking in the skyline, the Mag Mile is an essential Chicago experience.
– Spot the Icons as You Go
Pause at the Wrigley Building to admire its white terracotta and at Tribune Tower to see the neo-Gothic crown; be sure to look for the embedded stones out front.
– Shop Water Tower Place and Its Historic Neighbors
Duck into Water Tower Place, then cross to the original Chicago Water Tower and Pumping Station—both famous survivors of the Great Chicago Fire.
– Finish by the Lake
When you reach Oak Street, walk a block or two east to feel the Lake Michigan breeze and watch runners stream along the lakefront path.
(Want to experience the Mag Mile and more without the hassle? The Lakefront Neighborhoods Bike Tour pedals past Michigan Avenue, through the Gold Coast, and into Lincoln Park—mixing local stories and skyline views along the way.)
Navy Pier and the Waterfront
– Navy Pier: Rides, Views, and Lakefront Energy
Stroll the wide promenades, pick up an easy snack, and ride the Centennial Wheel for a fresh angle on the skyline. Families will find plenty of room to roam, while couples can linger over casual dining with Lake Michigan as the backdrop.
– Chicago Shakespeare Theater
If you want to balance rides and views with performing arts, time your visit around a production at Chicago Shakespeare Theater and catch the Wheel’s lights afterward.
– Seasonal and Special Events
Summer brings fireworks, festivals, and live music; fall adds harvest pop-ups and weekend happenings; winter shifts indoors with markets and holiday programming; spring arrives with opening-week buzz and cool lakefront walks. Check Navy Pier’s calendar before you go so you can time a show or fireworks display.
(Bobby’s Ultimate City Bike Tour packs Navy Pier, Buckingham Fountain, Millennium Park, Museum Campus, Soldier Field, and more into a single ride—perfect for first-timers or anyone who wants to see the icons in one loop.)
Along the Water: Riverwalks, Architecture, and Kayaking
– Walk the Chicago Riverwalk
Follow the stepped path at water level for a calmer perspective on downtown; cafes, public art, and boat landings keep the scene lively without feeling frantic.
– Take an Architecture Boat Tour
Get a fast, engaging crash course in Chicago architecture and the engineering behind it—an ideal first-timer overview with unobstructed views up the canyons of the Chicago River.
(Prefer to stay on land? Our guides point out the same standout architecture from riverfront viewpoints—and add plenty of local stories you won’t get on the water.)
– Kayak on Lake Michigan
Want the skyline from water level? Kayaking on Lake Michigan gives you a totally different view—glide along the shoreline, watch the glass buildings reflect the light, and feel the open water stretch out behind you.(Bobby’s Bike Hike & Food Tours offers kayak rentals right at Ohio Street Beach—single or tandem—perfect for a quick paddle or a sunset session on the lake.)
– Pause on the Bridges for the Classic Shot
Step onto the movable bridges to capture postcard-worthy views downriver, then return to the Riverwalk for an easy exit.
– Wrap with a Sunset Sip
When golden hour hits, settle in at one of the Riverwalk’s best patios or open-air bars and soak up city lights as they dance across the water. There are plenty of places to linger with a drink—here are a few favorites for evening unwinding:
- City Winery: Perfect for wine lovers and live music fans; their riverside patio offers one of the best sunset views right on the water.
- Island Party Hut: Kick back with tropical drinks, games, and a relaxed vacation atmosphere (plus a small stretch of sandy beach).
- Taco Rio: For something livelier, swing by this Mexican eatery for margaritas, tacos, and a festive vibe along the river.
- The Northman Beer & Cider Garden: This outdoor spot is beloved for cider, local beers, and casual fare—great for groups, with picnic-style seating.
- Tiny Tapp & Café: Known for craft beers, creative cocktails, and shareable bites. Grab a seat facing the skyline or people-watch from their buzzy deck.
Most of these spots offer outdoor tables and waterfront views. Whether you want a glass of wine, local beer, or something casual, you’ll find plenty of choices to enjoy the end of your day as the skyline lights flicker to life.
Chicago From Above: Views You’ll Never Forget
– Skydeck Chicago and The Ledge
At Skydeck Chicago in Willis Tower (formerly the Sears Tower), you step out onto The Ledge—a glass box 1,353 feet above Wacker Drive—where the thrill meets a breathtaking view. The photos are absolutely worth it, and timed entry keeps lines moving so the experience feels easy. If you want even less guesswork, CityPASS helps you lock in a visiting window and glide right in.
– 360 CHICAGO Observation Deck (875 N. Michigan Avenue)
High inside the John Hancock Building—officially 875 N. Michigan Avenue—360 CHICAGO opens a cinematic sweep of city grid, lake, and sky. Aim for sunset so you can watch the lights ripple down Michigan Avenue, then linger as the skyline shifts into night mode and the water turns ink-blue below.
Chicago’s Museums: History, Science and Art
– Field Museum (Museum Campus)
The Field Museum blends blockbuster exhibits—SUE the T. rex among them—with thoughtful journeys through culture and nature. Because it anchors Museum Campus, you also get easy lake views and broad lawns for a between-gallery breather. Families can comfortably spend a half day here without running out of discoveries.
– Museum of Science and Industry
Down in Hyde Park, the Museum of Science and Industry turns imagination into room-sized adventures, from a captured WWII submarine to a walk-through heart and hands-on weather labs. It is playful, smart, and genuinely beloved. CityPASS covers this stop as well, which makes planning a multi-museum day that much simpler.
– Art Institute Revisited
Back downtown, it is worth repeating: the Art Institute of Chicago belongs on every first-timer’s list the way MoMA or the Met does in New York. The caliber is that high—only here the distances between galleries feel shorter, which makes lingering with favorites even easier.
Food, Jazz and Chicago After Dark
– What to Eat
When it comes to food, start classic. Try deep-dish pizza once and tavern-cut pizza twice. Add a Chicago-style hot dog (no ketchup) with sport peppers, then seek out an Italian beef and choose your destiny—dry, wet, or dipped, with hot or sweet peppers. For dessert, hunt down Garrett popcorn or a Rainbow Cone. Summer folds in night-market pop-ups and outdoor eats, while winter warms things up with spiced drinks and bustling indoor food halls.
(Our Bikes, Bites & Brews® Tour combines deep‑dish, hot dogs, and local sweets into a biking route that tastes like the city itself.)
– What to Hear
Chicago’s live music lineage runs deep, with blues joints that keep the grit, jazz rooms layered with history, and clubs that launch tomorrow’s headliners. The Green Mill swirls with old-school atmosphere, and Kingston Mines keeps guitars humming late into the night. You will also find performing arts across The Loop’s theaters and on neighborhood stages, so it is easy to pair dinner with a show.
(Ask your guide after any Bobby’s Bike Hike Tour for live‑music picks; we love pointing guests toward authentic blues and jazz spots.)
– Where to Wander
After dinner, pick a mood and take a walk. The Chicago Riverwalk turns into a ribbon of reflections, Navy Pier glows as the Centennial Wheel spins, and Michigan Avenue windows shine like a moving gallery. The city rewards an unhurried stroll.
Beyond Downtown: Chicago’s Neighborhoods
– Chinatown
Just a short CTA ride from downtown, Chinatown is a delicious deep dive into Chicago’s immigrant food traditions. Start along Wentworth Avenue for dim sum, noodle shops, and bakeries, then explore the Chinatown Gate, the Square, and nearby parks for photos and a breather between bites. It is an easy, family-friendly detour that pairs culture, history, and stellar menus in one compact walk.
(Bobby’s Bike Hike & Food Tours offers a Chinatown Food & Culture Walking Tour, where you’ll try multiple tastings and hear stories behind the neighborhood’s architecture, history, and dishes.)
– Lincoln Park and the Lakefront North Side
Lincoln Park Zoo is free, which makes it a reliable favorite for families. Pair your visit with the Conservatory’s palms and ferns, then loop the lakefront for skyline photos that never get old. Cafes cluster along the side streets, so a latte is always within a short walk.
(Our Lakefront Neighborhoods Bike Tour links the zoo, lakefront trail, beaches, and landmark neighborhoods into one smooth ride.)
– Wicker Park: The Milwaukee Ave Stretch
Ride (or walk) the Milwaukee Avenue corridor in Wicker Park and you’ll hit one of Chicago’s most creative food-and-nightlife routes. Indie coffee shops, microbreweries, vintage stores, and chef-driven restaurants line the avenue, offering a fresh, eclectic vibe around every corner. Weekends fill the area with bustling patios, impromptu sidewalk performances, and openings from local makers—making it the perfect urban spot to linger before dinner or a drink.
(Want to taste your way through this area? Bobby’s Bike Hike & Food Tours’ Westside Foodie Ride bikes this stretch and stops for tacos, pierogi, pizza, and local brews — a built-in neighborhood deep dive without any planning required.)
– Pilsen
Murals splash color across brick in Pilsen, where galleries and taquerias sit door to door. Do not miss the National Museum of Mexican Art—free, moving, and a masterclass in culture. The CTA makes it an easy hop and the vibe offers a very different slice of the city than downtown.
– Wrigleyville
Baseball fan or not, Wrigley Field feels like a pilgrimage. The surrounding bars carry game-day buzz almost year-round, while off-days feel like a neighborhood party that has simply quieted down. If you catch a matinee, you will still have daylight for a lake walk afterward.
Planning Your First Chicago Trip
When to Visit
Summer is a lakefront love letter with beaches, festivals, and sidewalk tables. Fall flips on gold light and crisp air. Winter layers on charm—twinkle lights in the trees, Christkindlmarket mugs, a low-sun glow—and New Year celebrations that spill from hotels into neighborhood bars. Spring brings park blooms and a locals-are-back energy. Whenever you land, check Choose Chicago for updated calendars and special events so you can time your must-see moments.
(Looking for a festive way to experience Chicago in winter? Bobby’s Bike Hike & Food Tours offers a popular Chicago-Style Holiday Hike: Season Sampling Food & Walking Tour that combines iconic holiday sights, delicious food, and seasonal cheer.)
How to Get Around
Downtown Chicago is wonderfully walkable, and the CTA’s elevated train (aka the L) and buses connect most of what you will want to see. Divvy bike-share docks dot the grid for one-way rides along Lake Michigan or the Chicago River. If you are stacking attractions, CityPASS shines by shrinking ticket lines and expanding your time actually doing. Most major sites are ADA-accessible, from the Riverwalk to Skydeck Chicago, so planning with different mobility needs in mind is straightforward.
(Many visitors choose a Bobby’s Bike Hike Tour as their first‑day orientation—it helps you map out what to do next.)
Tips for First-Time Visitors
Because weather can shift quickly near the lake, pack layers and plan for a breeze. Book key sights in advance—Skydeck Chicago, boat tours, and hot restaurants go fast—then wear comfortable shoes so you can move easily between lobbies, bridges, and parks. If you balance the icons with a couple of neighborhoods, you will feel the full city rhythm the Midwest is proud of.
The Best Way to See It All: Bobby’s Bike Hike & Food Tours
After a list like that, the question isn’t “what’s there to do?”—it’s “how do we fit it in?” That’s where we come in. At Bobby’s Bike Hike & Food Tours, we stitch together the lakefront, the landmarks, and the flavors into one smooth arc, so you can spend your time looking up instead of looking at maps.
Prefer to keep it simple on foot? Our walking routes thread downtown Chicago icons with bites that locals actually crave. Want more ground and bigger views? Our bike tours ride protected paths along the lakefront and the Chicago Riverwalk, pause for photos, then roll to neighborhoods where the stories (and snacks) get good. Guides handle the pacing, pepper in Chicago architecture highlights, and point you to a perfect nightcap when we’re done.
Traveling with kids or a crew? We keep things family-friendly, offer e-bike upgrades on select rides, and can shape a private tour around your pace and priorities. If you’ve only got a weekend, we’ll help you cover the best things to do with room left over for serendipity. If you’re here longer, we’ll get you oriented fast so the rest of your plan feels easy.
Ready to ride (or stroll) the Windy City? Book a Bobby’s Bike Hike & Food Tour and turn a first visit into a story: Millennium Park in the morning, riverside bridges by midday, neighborhood eats by afternoon, and lake-lit views as the city glows. One day, many angles, and exactly how Chicago your first trip to Chicago should be.
