That resilience defines the city’s pulse, a gritty, welcoming warmth where strangers share cab rides and deep-dish slices with equal ease. Today, Chicago stands not just as a architectural marvel but as a living room for the world, inviting you to wander its brick-lined alleys and feel the enduring spirit of reinvention in every breeze off Lake Michigan.
Do Chicago the way locals do: start slow at Waterfall Glen Forest Preserve, eat where the regulars do at Kitchen + Kocktails By Kevin Kelley - Chicago, let the evening run long at Three Dots and a Dash.
Top things to do in Chicago
Ranked by rating and review volume. These earn their hype. Booking links may earn Roam a commission, at no cost to you.
1
Millennium Park
24.5-acre green space with a video display, the reflective "Bean" sculpture & an outdoor theater.
Check tours & tickets2
Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
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The Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
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Griffin Museum of Science and Industry
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
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Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
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Skydeck Chicago
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
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Chicago Riverwalk
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
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The Museum Campus
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
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Shedd Aquarium
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
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The Morton Arboretum
Diverse 1,700-acre nature preserve with a maze garden & tram plus picnicking, hiking & biking.
Check tours & ticketsWhere to eat
Local favorites, not tourist traps.
11
Kitchen + Kocktails By Kevin Kelley - Chicago
Global comfort fare like fried chicken & waffles, plus cocktails, served in a flashy lounge setting.
Website12
Giordano's
Known for deep-dish pizza, this casual chain serves other classic Italian food, plus beer & wine.
Website13
Quartino Ristorante
Bustling, bi-level space where groups go for small & large plates plus cocktails & carafes of wine.
Website14
Ed Debevic's
Funky classic diner with 1950s decor serving American comfort food such as burgers & shakes.
Website15
Aba
Posh destination for elevated Mediterranean fare and cocktails, plus a lounge-style rooftop patio.
Website16
Portillo's & Barnelli's Chicago
Chicago-born chain for hot dogs, Italian beef sandwiches & more, plus beer & wine, in retro digs.
Website17
18
Gordon Ramsay Burger - Chicago
Trendy, celebrity-chef venture dishing up hefty, creative hamburgers with vegan options.
WebsiteHungry for more? Book a food tour or tasting in Chicago
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Tours worth booking ahead
These sell out, so lock them in early.
19
Tours & Boats Architecture Tours
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Wendella Tours & Cruises
Boat tour company started in 1935, offering river and lake cruises plus private boat rentals.
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Chicago Gangsters and Ghosts Tours
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Shoreline Sightseeing
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First Lady
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Chicago River Boat Architecture Tours
Check tours & ticketsGet outside
25
Waterfall Glen Forest Preserve
Wildlife & plant preservation area with glacial potholes, multi-use trails, fishing & picnicking.
Website26
Northerly Island Park
91-acre peninsula with skyline views, hiking, fishing & playing plus a fieldhouse & live music acts.
Website27
LaBagh Woods
This wooded area is a popular spot for nature observation & offers trails & picnic areas.
Website28
Schiller Woods
Fishing for bass & catfish, plus walking trails, picnic areas & roaming deer in protected woodland.
Website29
North Park Village Nature Center
46-acre nature preserve with hiking trails, a birding area & a center with educational programs.
WebsiteAfter dark
30
Three Dots and a Dash
Classic tropical cocktails, rums & house daiquiris in a retro Polynesian-style setting.
Website31
Gus' Sip & Dip
Website32
Cindy's Rooftop
Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
Website33
The Green Mill
Swinging sounds are on tap nightly, from big-name artists to local late-night jam sessions.
WebsiteEverything above is live data. Real ratings, opening hours, and photos, not AI guesswork. The planner turns it into your day, hour by hour.
The whole guide on one map
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