Top things to do in Chicago
Rainy-day theater tours, family action parks, and classic Chicago river outings all make sense today.
Chicago’s best-known experiences span the river, the stage, and a handful of family-friendly day trips. With rain in the forecast, it’s smart to mix indoor picks with one or two weather-dependent favorites worth booking ahead.
Best tours and standout experiences
A balanced mix of river classics, indoor outings, and family-friendly side trips
This lineup works best when you mix pace and setting: a grand theater, a splashy family stop, then a marquee Chicago cruise. For rainy weather, keep the indoor picks near the top of your list and save the boats for breaks in the forecast.
The Chicago Theatre Tour Experience
A backstage-style look inside one of the city’s best-known landmarks. A strong rainy-day choice if you want architecture and history without a long commitment.
"Arrive light and a little early; access can change when shows are in progress."

The Forge Adventure Park & Ziplines
A former quarry turned action park with ropes, climbing, trails, and more. Best for active families and groups who want a full outing rather than a quick stop.
"Best as a dedicated excursion; plan extra transit time from central Chicago."

First Lady
$$One of Chicago’s signature river cruises, known for architecture-focused narration. Ideal for first-time visitors who want the city explained while they sightsee.
"Best on a dry spell; bring a layer even in June on the water."

The Water Works Indoor Water Park
A practical family fallback for wet weather, with slides, rapids, and play areas under cover. Best for kids who need to burn off energy.
"A better fit for a family day than a city-center sightseeing schedule."

Medieval Times Dinner & Tournament
$$Dinner theater with jousting, falconry, and full-on pageantry. A lively evening option for families, birthday groups, or anyone leaning into campy fun.
"Best booked as an evening anchor, especially if your group wants dinner and entertainment together."

Segal Visitors Center
A quieter pick on Northwestern’s lakefront campus, with visitor information and broad views. Best for prospective students or travelers exploring beyond downtown.
"Makes most sense when paired with a wider Evanston outing."

Wendella Tours & Cruises
A long-running Chicago boat operator offering river and lake cruises. Good for travelers who want classic sightseeing with flexible cruise styles.
"Choose this when flexibility matters more than a single flagship tour format."

Ninja Kidz Action Park Hammond, IN
A high-energy indoor play spot with obstacle-style fun, games, and climbing. Best for families with children who need room to run.
"Best for kid-focused itineraries rather than short downtown stays."
Chicago Architecture Center River Cruise Aboard First Lady
A ticketed architecture cruise that rewards visitors who like context with their skyline views. Book ahead if this is a must-do.
"Popular departures often fill up; arrive early and keep your camera handy."

Cadillac Palace Theatre
A beautifully ornate Loop theater known for major stage productions. Choose it for a polished night out in the theater district.
"Ideal after dinner in the Loop; check the current production before planning around it."
Classic Stadium Tour
A straightforward Soldier Field tour for sports fans and curious visitors alike. Best if you want a break from museums and downtown architecture.
"Most rewarding if your group already has some interest in the venue."

Sky Zone Trampoline Park
An indoor trampoline park with freestyle jumping and active games. Handy for families who need a flexible, weather-proof outing.
"Best as a short, easy family stop rather than an all-day excursion."

Rainbow Falls Waterpark
A seasonal outdoor water park with slides, pools, and a lazy river feel. Best saved for warmer, drier weather and family-heavy itineraries.
"Better for a sunny suburban day than for today’s wet forecast."
Top places to explore
A varied mix of skyline lookouts, gardens, museums, lakefront walks and family-friendly detours.
With rain in the forecast, it helps to mix quick outdoor icons with indoor backups and flexible half-day outings. This lineup balances classic downtown sights with bigger nature and family options farther out.

Millennium Park
Chicago’s best-known downtown green space pairs public art, gardens and a major outdoor performance venue. It works well as a first stop because so much of the city radiates out from here.
"Best as a flexible daytime anchor near several other central sights."

Adler Planetarium Skyline Walk
For pure skyline drama, few spots beat this open lakefront viewpoint. It’s especially rewarding at sunrise, sunset, or after a museum stop nearby.
"Go near sunset if the weather cooperates; the skyline glow is the main event."

360 CHICAGO
A polished observation deck with sweeping lake-and-city views from high above Michigan Avenue. It’s a good fit for sunset or an evening slot.
"A smart choice if you want city views without much walking."

Chicago Riverwalk
This riverside promenade is one of the best ways to feel downtown Chicago at street level. Go for architecture views, people-watching and a gentler city pace.
"Best for a weather break between indoor stops, not necessarily an all-day plan in rain."

Skydeck Chicago
The Willis Tower’s observation deck is the high-altitude option for big views and memorable photos. It appeals most to first-time visitors chasing a signature Chicago moment.
"Choose this over 360 CHICAGO if the photo moment matters most."

North Avenue Beach Pier
Come here for one of the city’s best skyline-and-lake views with an energetic beach backdrop. It works well for a walk, a pause, or sunset photos.
"A smart pick for photos, especially when you want lake and skyline in one frame."

Chicago Botanic Garden
385 acres of landscaped gardens displaying millions of plants & flowers in a variety of settings.
"Best for unrushed wandering; wear comfortable shoes and give yourself time to explore beyond the main displays."

Kohl Children's Museum
Permanent & rotating exhibits are found at this museum catering to kids from birth to age 8.
"Best with children under 8; bring a change of clothes if water play is on the agenda."

Lincoln Park Zoo
Small, free zoo with lions, primates, reptiles, a children's area & an interactive farm exhibit.
"Pair it with a walk through Lincoln Park for an easy half-day near the lake."

University of Chicago: Hyde Park
University
"Best approached as a walkable neighborhood stop, not a ticketed attraction."

Lilacia Park
A small historic garden famous for lilacs and tulips, with walking paths and picnic space. In bloom season, it feels far grander than its size.
"Timing matters here—check bloom season if flowers are the main reason for your visit."

Pelican Harbor Indoor/Outdoor Aquatic Park, Bolingbrook Park District
Year-round water park with a river, slides, sprays & a lap pool plus concessions & a picnic area.
"Good backup for bad-weather days; expect the experience to vary a bit during busier periods."

Galloping Ghost Arcade
Old-school arcade offering a wide array of retro & new games & special pricing for unlimited play.
"Ideal for rainy days and friendly competition; the flat-fee format rewards lingering."

Altitude Chicago Trampoline Park
An energetic kid-focused stop with trampolines, dodgeball, and plenty of indoor-style activity. Useful when younger travelers need to jump, climb, and move.
"Best as a practical child-friendly break, especially on a mixed-age trip."

Lake Katherine Nature Center
Center with gardens, a waterfall, lakeside trails & native trees, plus regular family activities.
"Curator pick for travelers interested in nature preserve."

Adler Planetarium
A strong rainy-day pick with space exhibits, sky shows and one of the city’s loveliest lakefront settings. Families and curious adults both get plenty from it.
"Combine with the skyline walk if showers ease between indoor exhibits."

Lakefront Trail - North Trailhead - Ardmore Ave - 5800 N
Cycling lanes, picnic areas, and a beach highlight this park featuring a lake for swimming and kid-friendly hikes.
"Best used as a launch point—pick a direction and let the lakefront set the pace."

Cloud Gate
Chicago’s most famous public artwork still earns a stop, especially if you’re already in Millennium Park. It’s quick, central, and great for first-time visitors.
"Best treated as a short detour, not a standalone outing."

The Morton Arboretum
A major tree-focused landscape with trails, gardens, and enough room to spend a full day outdoors. Excellent for walkers, families, and anyone wanting a substantial escape.
"Choose this for a full outing, not a quick stop on the way elsewhere."

Waterfall Glen Forest Preserve
Wildlife & plant preservation area with glacial potholes, multi-use trails, fishing & picnicking.
"Bring water and plan your route—the trail network invites longer outings than you might expect."

Lincoln Park
Expansive outdoor urban refuge containing its own zoo, conservatory, theater, museums & playgrounds.
"Curator pick for travelers interested in city park."

Chicago Yacht Club
Waterfront yacht club offering members upscale dining, events, and lake views.
"More exclusive than casual—best for planned visits rather than spontaneous drop-ins."

Sky Zone Trampoline Park
Chain of indoor trampoline parks featuring freestyle bouncing, dodgeball, fitness programs & more.
"Best when you want a high-energy indoor outing without much planning."

Puttshack - Oakbrook
Mini-golf establishment pairing modern technology with fun courses, and offering food and drinks.
"Go off-peak if you want a smoother round and less waiting."

St. Peter's Catholic Church
Visitors say this church features beautiful architecture, stunning stained glass, and a granite altar with carved details of the holy family. They also highlight the welcoming and peaceful atmosphere, offering a serene place for prayer and reflection. Others also mention the frequent confession hours and the convenient gift shop.
"Worth ducking into if you need a peaceful reset in the Loop."

Visitor Center
Expansive botanical garden featuring plants and trees along with art installations and trails for hiking and biking.
"Come here when you want a full outdoor day without needing expert planning."

Chicago Cultural Center
A reliable free indoor stop with grand historic interiors and rotating arts programming. It’s ideal when you want beauty without committing to a long museum visit.
"An excellent indoor pairing with Millennium Park and Cloud Gate."

Graceland Cemetery
Scenic burial grounds with many trees, plus tours of the tombs & headstones of notable figures.
"Curator pick for travelers interested in cemetery."

The Chicago Theatre
French Baroque-style 3,600-seat auditorium showcasing national musical & comedy acts since 1921.
"Book this when you want a classic Chicago night out indoors."

The Forge Adventure Park & Ziplines
Former quarry turned activity park with bike trails, rope courses & climbing walls, plus zip lines.
"Best for travelers who want to do something, not just look around."
Where to stay in Chicago
A balanced mix of downtown classics, design-forward stays, and resort-style options.
For a rainy Chicago stretch, these stays work well as bases in their own right—some polished and central, others better if you want space, amenities, or a distinct neighborhood mood.

Chicago Athletic Association - The Unbound Collection by Hyatt
$$$A characterful stay opposite Millennium Park, with dramatic historic interiors and lively public spaces. Come for the sense of place as much as the room key.
"Especially good if you want to walk to the Art Institute, the lakefront, and Loop sights."

Four Seasons Hotel Chicago
$$$An elegant high-rise choice for travelers who want polished service and strong lake or skyline views. It suits a splurge weekend or a family stay with extra comfort.
"A smart fit if you want easy access to the Magnificent Mile and a calm, upscale base."

Soho House Chicago
A West Loop stay with a strong social buzz, rooftop energy, and creative-club styling. Better for atmosphere seekers than anyone craving a hushed retreat.
"Works particularly well for a weekend centered on West Loop dinners and drinks."

JW Marriott Chicago
$$$A polished downtown base in a landmark building, with generous rooms and useful wellness perks. Good for business trips, rainy weekends, and travelers who like a calm, full-service hotel.
"A practical choice for train arrivals, downtown meetings, and museum-focused itineraries."

Eaglewood Resort & Spa
A resort-style option beyond the city core, with room to spread out and more on-site recreation than a typical downtown hotel. It makes sense for a drive-in stay or a low-key getaway.
"Best if you have a car and plan to make the hotel part of the trip, not just a sleeping base."

Union League Club
A traditional, club-like stay with old-school Chicago character and a strong central location. It will appeal most to travelers who appreciate heritage over trendiness.
"Choose this one for heritage charm rather than rooftop-scene energy."

Loews Chicago Hotel
$$$A sleek Streeterville stay with modern rooms, strong amenities, and a rooftop bar for city views. It’s an easy all-purpose choice for couples, families, or first-timers.
"A handy base for Navy Pier, the riverwalk area, and Magnificent Mile plans."

Schaumburg Convention Center
A practical suburban convention stay with meeting infrastructure and plenty of parking. It’s most useful for event attendance rather than a classic city break.
"More practical than atmospheric—ideal if Schaumburg is the reason for your trip."
Best outdoor picks for fair weather
A balanced mix of skyline walks, beaches, gardens, family outings, and bigger nature escapes.
When Chicago clears up, these are the outdoor spots worth building a day around. We’ve mixed easy central classics with farther-flung nature stops, so the list reads like real options rather than one long run of parks.

Chicago Riverwalk
A classic Chicago stroll with bridges, boats, skyline views, and plenty of places to pause for a drink or bite. Best for an easy downtown wander without needing a full plan.
"Ideal between Loop stops; late afternoon gives you the best mix of light and atmosphere."

Cloud Gate
Chicago’s most famous public artwork still earns a stop, especially if you’re already in Millennium Park. It’s quick, central, and great for first-time visitors.
"Best treated as a short detour, not a standalone outing."

Chicago Botanic Garden
A full-scale garden destination with themed areas, broad paths, and enough variety for a leisurely half day. Best for plant lovers and anyone wanting a quieter outing.
"Worth the trip if you want nature over skyline; allow at least half a day."

North Avenue Beach Pier
Come here for one of the city’s best skyline-and-lake views with an energetic beach backdrop. It works well for a walk, a pause, or sunset photos.
"A smart pick for photos, especially when you want lake and skyline in one frame."

Osaka Garden
A small, serene garden with bridges, water, and a gentler pace than the city center. Best for a reflective walk or quiet photos.
"Better for a quiet stroll than a big-ticket attraction checklist."

Brookfield Zoo Chicago
A strong family option with enough animal variety and space to fill most of a day. Good for kids, but not only for kids.
"Best when you have time to wander rather than trying to rush highlights."

Lurie Garden
A compact but beautifully designed garden tucked into Millennium Park. It’s ideal when you want greenery without leaving downtown.
"Perfect paired with Cloud Gate or a Loop museum afternoon."

Ping Tom Memorial Park
A relaxed riverfront park in Chinatown with pagoda-style details, playground space, and skyline views. Good for families and low-key walks.
"Best used as a scenic pause before or after exploring Chinatown."

Adler Planetarium Skyline Walk
For pure skyline drama, few spots beat this open lakefront viewpoint. It’s especially rewarding at sunrise, sunset, or after a museum stop nearby.
"Go near sunset if the weather cooperates; the skyline glow is the main event."

Cypress Cove Family Aquatic Park
A family-focused water park with slides, pools, splash features, and casual food on site. Best for a hot day with children who want active fun.
"Most useful for visitors with younger kids and a flexible suburban day."

Lakefront Trail - North Trailhead - Ardmore Ave - 5800 N
A practical entry point to one of Chicago’s best outdoor assets: miles of lakefront path for walking, cycling, and easy family time. Good if you want movement, not just sightseeing.
"Choose this when you want open space and motion more than a fixed attraction."

Jackson Park Cherry Blossoms
Best known in bloom season, but still a pleasant park outing with water, paths, and a calm South Side setting. A natural pairing with Osaka Garden.
"Most rewarding in spring, but still pleasant when paired with nearby garden stops."

Montrose Dog Friendly Area
One of the best picks in the city if your dog is traveling with you. It’s social, sandy, and made for splashing around by the lake.
"Most valuable if your trip includes a pet; otherwise prioritize other lakefront spots."

Whalon Lake
A roomy suburban nature escape with trails, water, and picnic-friendly space. Best for visitors who want a quieter outdoor day beyond the city core.
"Best if you have a car and want a break from downtown density."

Altitude Chicago Trampoline Park
An energetic kid-focused stop with trampolines, dodgeball, and plenty of indoor-style activity. Useful when younger travelers need to jump, climb, and move.
"Best as a practical child-friendly break, especially on a mixed-age trip."

Blackwell Forest Preserve
A bigger nature day with trails, fishing, boating, and room to spread out. Good for repeat visitors or anyone wanting more than an urban park.
"Good for repeat Chicago visitors who want a fuller outdoors day beyond the lakefront."

Knoch Knolls Park
A versatile park with trails, disc golf, river access, and enough variety for families or casual outdoor time. It’s a practical suburban option rather than a landmark stop.
"Best added to a Naperville-area day rather than treated as a city highlight."

The Morton Arboretum
A major tree-focused landscape with trails, gardens, and enough room to spend a full day outdoors. Excellent for walkers, families, and anyone wanting a substantial escape.
"Choose this for a full outing, not a quick stop on the way elsewhere."

Clarence F. Buckingham Memorial Fountain
Grant Park’s monumental 1927 fountain stages dramatic hourly water displays and evening light shows. It’s one of the city’s classic photo stops.
"Time your visit to catch the water show for the full effect."

The 606
Created on a former rail line, this elevated, 2.7 mile landscaped trail draws runners & bikers.
"Good for a low-cost, flexible outing at almost any pace."

Fort Sheridan Forest Preserve
A lakefront preserve with rolling trails, wildflowers, beach access, and traces of the historic fort. It feels pleasantly removed from the city.
"Curator pick for travelers interested in nature preserve."

Walsh (John) Park
Green space with a large play structure, swings, a grassy field & a dog-friendly area.
"Curator pick for travelers interested in city park."

St. James Farm Forest Preserve
Hikers, bikers & horseback riders can explore a protected area of woodlands, prairies & wetlands.
"Curator pick for travelers interested in nature preserve."

Rainbow Falls Waterpark
Swim-season attraction with a tropical theme & numerous pools & rides including a huge 4-way slide.
"Go early for shorter slide lines and easier seating, especially on hot weekends."