Five ways into Chicago, without getting lost in endless lists. The deep dish and the Italian beef, the architecture and the lakefront, the hidden bars and the escapes just outside the city, cut down to the five that matter in each.
Best Value9 free, skimmable Chicago lists. No sign-up, no paywall.
EatThe five classic Chicago foods, deep-dish pizza, Italian beef, the Chicago-style hot dog, the jibarito, and the Maxwell Street Polish.
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SipThe five best rooftop bars in Chicago, Cindy's over Millennium Park, LH Rooftop at LondonHouse, Z Bar, Cerise, and the J. Parker.
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ExploreFive Chicago neighborhoods that reward an aimless afternoon, Wicker Park, Logan Square, Pilsen, Lincoln Park, and Andersonville.
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EscapeThe five best beaches in Chicago, North Avenue Beach, Oak Street Beach, Montrose Beach, 12th Street Beach, and Ohio Street Beach.
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ExperienceThe five best museums in Chicago, the Art Institute, the Field Museum, the Museum of Science and Industry, the Shedd Aquarium, and the Adler Planetarium.
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ExperienceFive Chicago experiences that cost nothing, Millennium Park and the Bean, the Lincoln Park Zoo, the 606 trail, the Lakefront Trail, and the Chicago Cultural Center.
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DiscoverFive Chicago hidden gems, the Garfield Park Conservatory, the Rookery light court, the Chicago Pedway, Palmisano Park, and the Bahá'í House of Worship.
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DiscoverThe five best shopping neighborhoods in Chicago, the Magnificent Mile, State Street, Wicker Park, the West Loop, and Andersonville.
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StayFive iconic Chicago hotels worth seeing even if you're not staying, the Palmer House, the Drake, the Chicago Athletic Association, the Blackstone, and the Chicago Motor Club.
Read Free Five →Walk to the sights, sleep on top of every train line.
Best for: First trips, sightseeing, and transit to everywhereExplore picks →The best food-and-nightlife base, just over the river.
Best for: Eaters and drinkers who still want to walk everywhereExplore picks →Lakefront glamour at the top of the Magnificent Mile.
Best for: A romantic or upscale trip with old-Chicago eleganceExplore picks →The Mag Mile, Navy Pier and the lake on your doorstep.
Best for: Families and first-timers who want the big sights closeExplore picks →Local, cool, and one Blue Line stop from downtown.
Best for: Repeat visitors who want a real neighbourhood and better valueExplore picks →Ready-to-use plans with timing, reservations, insider tips, an interactive map, and a printable PDF.
First-Timer's
A first trip to Chicago, cut to the five decisions that shape it: where to stay, what to eat, what to do, when to go, and getting around.
Date Night
Five complete Chicago evenings, dinner, an after-spot, a step-by-step plan, and the detail that makes the night land.
Brunch
Five Chicago brunches worth the wait, one per neighbourhood, with what to order and exactly how to beat the line.
Hidden Bars
Five hidden Chicago bars worth the hunt, a basement below a fire-surviving tavern, a bordello behind a restaurant, an eight-seat spirits vault, a neon room behind a takeout counter, and a bar behind a barbershop.
Special Occasion Dining
Five Chicago restaurants worth a milestone, the three-Michelin-star icon, two two-star tasting rooms, a legendary fine-Mexican table, and a reasonably-priced tasting menu. With how far ahead to book.
Day Trips
Five day trips from Chicago worth the ride, from a whole Great Lakes city and a national-park lakeshore to canyon waterfalls, a preserved river town, and a lake resort. With how to get to each, what to book, and how long it really takes.
Where to Stay
Where to stay in Chicago, the five best neighbourhoods to base yourself, matched to how you travel: the Loop, River North, the Gold Coast, Streeterville, and Wicker Park. With the honest trade-off for each.
Every recommendation from the Chicago guides, mapped by neighborhood and category.
Preview only, unlock the full interactive, saveable map with any Chicago guide.
Tours and experiences that pair perfectly with our Chicago recommendations.
The city’s skyline story, told from the water.
Browse →Deep dish, hot dogs, and neighborhood classics with a guide.
Browse →Legendary improv stages and blues clubs.
Browse →Browse All Chicago Experiences
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