United States · Illinois
Plan your Chicago trip
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01Your itinerary
02Where to stay
The Loop
Best for first-timers and sightseeing on footDowntown proper — skyscrapers, the theatre district, Millennium Park and the Art Institute all within walking distance. The most convenient base for a first visit built around the headline sights, though it quiets down noticeably at night.
A high-rise hotel overlooking Millennium Park
Look for upper floors facing the park and lake for a skyline view that does most of the work for you.
$$$A converted historic office tower near the theatre district
Several of the Loop's grand early-twentieth-century office buildings have been converted into hotels, putting you inside the architecture rather than just looking at it.
$$$$River North
Best for food-focused trips and nightlifeThe densest concentration of restaurants and nightlife downtown, a short walk from the Loop and the Magnificent Mile, with a genuinely lively evening scene that the Loop itself lacks.
A boutique hotel near the Chicago River
Being steps from the river puts you within easy reach of the architecture cruise docks and the restaurant density of the neighbourhood.
$$$Lincoln Park
Best for families and repeat visitors wanting a quieter baseA leafy, residential lakefront neighbourhood with a free zoo, beach access and a genuinely local, less touristy pace, a short 'L' ride or bike from downtown.
A boutique hotel near the lakefront trail
Staying here trades a few minutes' commute downtown for direct access to the park, the zoo and the beach on your doorstep.
$$Wicker Park & Bucktown
Best for younger travellers and a local, non-touristy stayThe city's creative and nightlife hub — independent shops, live music, and a dense bar and restaurant scene with genuine neighbourhood character rather than a downtown-adjacent version of it.
A design-led boutique hotel near the 606 trail
Puts you within walking distance of the elevated park and the neighbourhood's bar and restaurant density, a short 'L' ride from downtown.
$$Affiliate notePostcardRoute is reader-supported. Some links to Booking.com (stays, flights, car hire, tickets and tours, airport transfers) are affiliate links, tracked through CJ Affiliate: if you book through them we may earn a small commission at no extra cost to you. We only recommend places we would send a friend.
03Tickets & tours
The Art Institute of Chicago
One of the great encyclopedic art museums in the United States, holding the world's best collection of Impressionist and Post-Impressionist painting…
Tip Go straight to the second floor Impressionist galleries first if crowds are a concern — the queue builds there before anywhere else in the building.
Millennium Park and Cloud Gate
The free public park that gave the city its most photographed object, the mirror-polished steel sculpture known universally as 'the Bean', plus the…
Tip Visit at sunrise for photos of the Bean without a crowd of a hundred people also trying to get the same shot.
Willis Tower Skydeck
The 103rd-floor observation deck of the building that held the title of world's tallest for nearly twenty-five years, with glass ledge boxes that let…
Tip Book a timed-entry ticket online in advance; walk-up queues on a clear weekend afternoon can run well over an hour.
Chicago Architecture Center river cruise
A ninety-minute boat tour along the Chicago River narrated by trained architecture-literate docents, widely considered one of the best introductions…
Tip Book the First Lady or Chicago's First Lady Cruises option specifically and sit on the side facing the newer riverfront towers for the best skyline angles.
Navy Pier and the lakefront
A century-old pier turned entertainment complex with a Ferris wheel, gardens and boat launches, functioning mostly as the gateway to the wider…
Tip Skip the pier's interior shops and head straight for a bike rental to actually experience what makes the lakefront worth the trip.
Museum of Science and Industry
Housed in the sole surviving building from the 1893 World's Columbian Exposition, home to a real German U-boat, a coal mine you walk through, and…
Tip Budget a full half-day minimum; the building is enormous and the good exhibits are spread across multiple wings.
Wrigley Field
The second-oldest ballpark in Major League Baseball, opened in 1914, still ringed by hand-turned scoreboard operators and the ivy-covered outfield…
Tip A rooftop seat on one of the buildings across Waveland or Sheffield Avenue is a genuinely different, and often cheaper, way to watch a game.
The 606 and Wicker Park
An elevated former rail line converted into a 4.3-kilometre linear park and cycling trail through the Northwest Side, running directly past the…
Tip Enter near Damen Avenue and walk east toward Humboldt Park for the quieter, less crowded half of the trail.
National Museum of Mexican Art
The largest Latino arts institution in the country and the anchor of Pilsen's cultural identity, with free admission and a permanent collection…
Tip Pair it with a walk down 16th Street to see the neighbourhood's dense concentration of murals before or after the visit.
Day trips from Chicago
Oak Park
A short 'L' ride west to the suburb where Frank Lloyd Wright built his home and studio and designed more than two dozen buildings, plus Ernest…
Day tripIndiana Dunes National Park
Roughly an hour southeast by car or the South Shore Line train, a genuine sand-dune landscape along Lake Michigan's southern shore with hiking trails…
Day tripGalena
A well-preserved nineteenth-century river town about three hours west near the Mississippi, with brick storefronts and Ulysses S.
Day tripEverything to do in Chicago
Skip-the-line tickets, guided tours and day trips, all in one place on Booking.com.
04Getting there & around
Getting around
The Loop and its immediate surrounding neighbourhoods are genuinely walkable, and the lakefront trail — nearly thirty kilometres of continuous, mostly car-free path running the length of the city — is one of the best urban walks or bike rides in the country, connecting neighbourhood after neighbourhood without a single traffic…
Flights
Compare fares into Chicago and pick dates that suit the days you planned.
Airport transfers
Book a private or shared ride from the airport so the first evening starts at your door, not at a ticket queue.
Car hire from Chicago
Only worth it for day trips beyond the city — in town, the plan above works on foot and public transport.
Affiliate notePostcardRoute is reader-supported. Some links to Booking.com (stays, flights, car hire, tickets and tours, airport transfers) are affiliate links, tracked through CJ Affiliate: if you book through them we may earn a small commission at no extra cost to you. We only recommend places we would send a friend.