Planning things to do in Chicago?
It’s easy to default to Navy Pier and the Skydeck.
But visitors often miss the city’s neighborhoods, music clubs, and free cultural spots that locals actually love.
This guide focuses on authentic, offbeat experiences—from conservatories to rooftop bars—that show a different side of the city.
You’ll discover 13 unique activities beyond the typical tourist trail that are doable today or this weekend.
You’ll get practical tips on where to go, how long things take, and which options are free or family-friendly.
Read on to plan a Chicago visit that’s more local, relaxed, and memorable than the standard sightseeing itinerary.
What are the best things to do in Chicago
Well, here’s the thing: pick a neighborhood to explore rather than chasing every landmark.
Start with what you want—architecture, food, music, or parks. Search for things to do in Chicago that match your mood.
Take a river cruise or a Chicago architecture tour to see iconic buildings from the water. Visit the Millennium Park Chicago plaza for public art and people watching.
Walk sections of the lakefront and end at Navy Pier Chicago if you want rides and views.
Timing makes a big difference. Go for tours in late afternoon for softer light and thinner crowds.
Reserve popular experiences like the Willis Tower Skydeck or guided Chicago food tours in advance.
Find free things to do in Chicago by visiting Garfield Park Conservatory, Lincoln Park Zoo, and the Chicago Cultural Center. You can spend a whole day on no-cost attractions and still see top chicago attractions.
Look for live jazz at intimate clubs and for rooftop bars in River North to sample chicago nightlife. Bring comfortable shoes—you’ll walk a lot.
Plan a half-day route now: pick a neighborhood, book one paid tour, and add one free stop. You’ll leave with a clearer sense of local life and real Chicago activities.
13 unique Chicago activities beyond the tourist spots
Explore the Underground Pedway and Downtown Secrets
The 2-hour guided Pedway tour reveals Chicago’s hidden core. The tour exposes an underground tunnel system full of stained glass and odd architecture.
You walk through passages below the Loop that most visitors never see. The guide points out an old underground swimming pool beneath a hotel and ornate mosaics.
You cover about one mile of corridors.
I’d say this is a top pick for things to do in Chicago. I’ve taken it and learned local history you won’t find in guidebooks.
Book the guided two-hour tour on GetYourGuide to secure a spot. The secret downtown passages make for memorable photos and unique stories.
Bring comfortable shoes and a light jacket. Decide now to add this to your Chicago sightseeing list.
Discover Garfield Park Conservatory
Visit Garfield Park Conservatory for a free, year-round escape into exotic plants and glass architecture. It ranks among the best things to do in Chicago for quiet, indoor exploration.
The conservatory covers about 4.5 acres of greenhouse space. Explore the Palm House, Desert House, fern room, and seasonal flower shows.
The setting feels like an exotic plants showcase beneath stunning glass structures.
We time visits for late morning to avoid crowds. The light through the glass makes photos pop and kids stay curious.
Plan 60–90 minutes. This is one of the top free things to do in Chicago and a solid indoor activity for rainy days.
Add it to your Chicago itinerary and confirm visit times before you go.
Experience live jazz at the Jazz Showcase
The Jazz Showcase delivers a true Chicago jazz night. The club opened in 1947 by Joe Segal and remains the city’s most historic jazz club near downtown.
The small room makes the music hit harder. You feel every note up close.
Expect straight-ahead, bebop, and modern sets. Shows run most nights with late sets on weekends.
Tickets often cost $20–45 depending on the act.
Buy on the club website and arrive early for seating. The bar serves small plates and cocktails.
Weekends sell out faster. Plan your evening and leave room for a late drink.
This ranks among the best things to do in Chicago for music lovers, couples, and local nightlife fans.
Pick a date and book your tickets today.
Visit the Richard H. Driehaus Museum
Visit the Richard H. Driehaus Museum for an intimate look at Gilded Age mansion design. You’ll see ornate rooms, stained glass, and the decorative arts collection in a compact space.
Budget 45–60 minutes for the visit. An hour lets you absorb details without feeling rushed.
The house opened as the museum in 2008 and sits in a restored late‑19th‑century mansion. The layout creates an intimate opulent setting that contrasts with larger Chicago attractions.
This visit ranks high among things to do in Chicago for adults, couples, and anyone who loves chicago museums. Buy tickets online or go midweek to skip lines and enjoy the rooms at your own pace.
Tour Graceland Cemetery
Touring Graceland Cemetery offers a peaceful, revealing stop on your Chicago sightseeing list. Walk over 120 acres of monuments and sculpted graves.
You’ll find Ludwig Mies van der Rohe, Ernie Banks, and George Pullman buried here.
Admire ornate mausoleums and landscape design that reads like outdoor museum space. The site highlights notable Chicago attractions and local history.
This is one of the best things to do in Chicago for architecture fans and history lovers. Bring a map or download a self-guided tour PDF to guide your visit.
Look for the Graceland Cemetery tour markers and stop at standout pieces of Chicago funerary architecture. Plan 45–90 minutes for a focused walk.
Your next step: add this to your list of things to do in chicago today and go explore.
Attend a Candlelight concert in historic venues
A Candlelight concert makes for a memorable night. Classical music and contemporary favorites fill Chicago’s most beautiful spaces.
The room glows from hundreds of candles, creating an intimate atmosphere.
Shows usually run 60–90 minutes in churches, theaters, or conservatories. They make great romantic things to do in chicago or solo outings.
The candlelit focus makes each piece feel larger. You’ll leave moved.
Ticket prices vary, so buy early—shows often sell out.
They often program film scores and pop arrangements. Expect reserved seating and printed programs.
Many concerts appear near Millennium Park or Navy Pier.
This counts as one of the best things to do in chicago for couples. Look for family-friendly times for things to do in chicago with kids.
Prices start around $20 to $45, depending on venue.
Book tickets from venue pages or authorized sellers and secure your seat online.
Skate at Maggie Daley Ice Ribbon
Skating the Maggie Daley Ice Ribbon offers a unique outdoor experience. Skate a winding quarter mile ribbon that hugs the park.
Glide under skyscrapers and enjoy stunning skyline views.
The layout delivers an alpine city experience unlike traditional rinks. It works great for couples seeking romantic things to do in Chicago.
Families find it fun for things to do in Chicago with kids.
The loop measures a quarter mile, so four laps equal one mile. Skating burns about 300 to 500 calories per hour for moderate effort.
Rent skates onsite or bring your own. Rent skate aids for toddlers and beginners.
Reserve timed entry during weekends and holidays. Go at sunset for glow or weekday mornings for quiet.
Decide when you’ll go and book tickets now.
Take a themed architecture walking tour
Take a themed architecture walking tour to see Chicago’s layers up close. Tours cover Early Skyscrapers, Art Deco gems and houses of worship across neighborhoods.
A 90–120 minute route works well for new visitors. Group sizes run 8–20 people and prices range $0–$40 depending on guide and route.
These tours make things to do in chicago feel local and memorable.
You learn design details, social history, and the stories behind Tribune Tower and other landmarks. The experience improves your chicago sightseeing and your sense of place.
|
Tour Theme |
Duration |
Price Range |
Best For |
|---|---|---|---|
|
Early Skyscrapers |
90–120 min |
$20–$40 |
Architecture fans |
|
Art Deco |
90 min |
$25–$40 |
Design enthusiasts |
|
Houses of Worship |
120 min |
Free–$30 |
History buffs |
|
African-American Landmarks |
90–120 min |
$20–$35 |
Cultural explorers |
Pick a theme that matches your interests. Book a small-group tour or join a free community walk.
Bring water, layers, and sturdy shoes.
Choose a morning slot to avoid crowds and book your tour now. Your next step: decide the neighborhood and reserve a spot.
Enjoy rooftop experiences at the Godfrey Hotel
The Godfrey Hotel rooftop offers skyline views and a relaxed vibe. Relax at Chicago’s largest indoor-outdoor rooftop in River North.
The space has a retractable roof and seasonal installations that change mood and light. You can sip a cocktail, dine, or wander the terrace for sweeping panoramic city views.
This spot ranks among the best things to do in Chicago. The rooftop works as an indoor activity Chicago visitors choose when weather is fickle.
Plan a night out for chicago nightlife or a romantic evening. Book ahead to secure a table.
Tip: aim for sunset and arrive early to claim a terrace seat. Bring a light jacket.
Check the events calendar for seasonal pop-ups and DJs.
Explore the Chicago Cultural Center
Visiting the Chicago Cultural Center reveals art and architecture worth your time. Join the free guided tours to learn local history and hidden stories.
The building hosts Tiffany domes that rank among the largest of their kind.
You’ll see rotating exhibitions that highlight Chicago artists and cultural programs. This site ranks high among Chicago attractions.
It offers free things to do in Chicago. You can catch free concerts and family programs.
The mosaics and music make it a must.
The center suits families, couples, solo travelers seeking calm indoor activities in Chicago. Plan 45 to 90 minutes for a solid visit.
Check event schedules for concerts or film screenings.
Pick a morning slot to avoid crowds. Pair this stop with nearby Millennium Park or a Chicago architecture tour.
Kayak on the Chicago River
Kayaking the Chicago River is one of the best things to do in Chicago for a downtown Chicago view. You pass iconic bridges and skyscrapers on trips that run 60–90 minutes.
Pick a guided tour for stories about architecture. Rent a kayak if you want freedom to explore at your pace.
Pack a light jacket, sunscreen, and a dry bag.
Launch sites cluster near the Riverwalk and Merchandise Mart. Ever wondered what the city looks like from water level?
We prefer guided morning launches for calm water and better photos. Early starts reveal details you miss from shore.
Avoid peak midday on busy summer weekends. Book 24 hours ahead for popular time slots.
Compare this with other waterfront trips like things to do in Funchal to decide the style you like.
Discover public art installations throughout the city
Hunting Chicago’s outdoor art beyond Cloud Gate reveals the city’s creative pulse. Find murals, sculptures, and installations across Pilsen, Wicker Park, and the Loop.
Look for public art installations on building facades and in pocket parks. You can spot dozens of pieces in a two-hour walk.
Use your phone to map murals and public sculptures as you go.
Pilsen street murals deliver the strongest local voice. Expect bold colors, cultural themes, and large-scale works near 16th Street and the National Museum of Mexican Art.
Start at Millennium Park Chicago to see Cloud Gate, walk into the Loop for plaza sculptures, and end in Wicker Park for neighborhood pieces. Set aside two hours.
Pick one neighborhood and explore on foot or join a guided mural tour to maximize your time.
Visit Lincoln Park Zoo
Visiting Lincoln Park Zoo offers a free, authentic Chicago experience. The zoo sits along the lake in Lincoln Park.
It offers diverse animal exhibits, gardens, and family programs.
The Regenstein Center shines. The prairie dog exhibit delights kids and adults.
Enjoy free admission year-round. Seasonal events and holiday lights draw local crowds.
This is one of the best things to do in Chicago with kids.
It ranks high among free things to do in Chicago. It’s a top chicago attraction for families.
Plan 1 to 2 hours for a relaxed visit.
If you plan winter travel beyond Chicago, check things to do in Rovaniemi for ideas.
Practical tip: visit early weekends or on weekdays to avoid lines. Pick your time and confirm event times online before you go.
Is the Chicago architecture tour worth it and how long does it take
Take the Chicago architecture river cruise—it delivers quick, high-value insight into the city. The standard cruise lasts about 75 minutes and moves along the main branch of the Chicago River.
Reserve a midday or morning slot to avoid crowds and catch steady light for photos. Want to actually understand what you’re looking at?
You should expect trained docents to narrate the route. Guides describe dates, architects, materials and design intent for buildings like Willis Tower and Tribune Tower.
Guides call out small features you miss from street level and point to layout choices that shaped the Loop. The boat gives wide sightlines and easy photo angles.
Most operators run 60 to 90 minute trips. Summer runs fill fast on weekends, so buy tickets early to lock a seat.
In my opinion, the narration turns the skyline into a story you can follow. New visitors, couples and families get clear context fast.
Architecture fans gain specific takeaways to chase on foot later.
Bring a light jacket for river breezes and a camera with a wide lens. Pick covered seating if rain threatens.
Book a 75-minute cruise for solid value and steady commentary. Enjoy the river cruise, listen to the expert guide, and expect great photos.
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What are the best free things to do in Chicago
Start with a few no-cost highlights to feel the city fast. (Your wallet will thank you!)
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Free Chicago experiences: Walk Millennium Park and pose by Cloud Gate for skyline photos.
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Lincoln Park Zoo: Visit one of North America’s oldest zoos with year-round free admission.
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Garfield Park Conservatory: Explore vast glass houses and tropical plants without an entry fee.
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Shedd Aquarium offers free or discounted days for Illinois residents; check their calendar for exact dates.
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Chicago Cultural Center runs free guided tours and hosts rotating art exhibits under its famous Tiffany dome.
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Hunt public art across Pilsen, the Loop, and Wicker Park for murals and sculptures on city streets.
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Stroll the Riverwalk for waterfront views and free outdoor events on summer weekends.
A slow morning at the conservatory followed by an afternoon of public art makes a perfect free day in the city. Pick one neighborhood and walk—you’ll see architecture, food carts, and local life without spending much.
Decide where to start and set a time. If you want more budget travel ideas, check our guide to things to do in Malacca for a short city break comparison.
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Best neighborhoods for Chicago nightlife
Choose River North for rooftop bars and Wicker Park for live music.
River North rooftop spots deliver skyline views and curated cocktails. The Godfrey Hotel rooftop has a retractable roof and city panoramas.
You can hit several rooftops in one night with short rides between venues.
Wicker Park music venues host indie bands, DJ nights, and open mics. Wicker Park offers the most electric late-night shows for young adults.
Expect small rooms, loud sets, and memorable local acts.
Logan Square and Pilsen serve authentic after-dark spots for craft beers, salsa bars, and late-night taquerias. Pick a neighborhood and hop between a cocktail bar and a music room to sample local culture.
For a contrast, see things to do in Hongdae for a similar neighborhood nightlife vibe.
Decide your vibe: rooftops, live music, or neighborhood dives. Plan one neighborhood per night to maximize walking and minimize transit.
That plan yields the best Chicago nightlife experience and uncovers real local favorites.
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