Towering skyscrapers, lakefront beaches, top-notch restaurants, and art galore – the Windy City will blow you away no matter what type of pursuit you’re looking for. Rise to the observation deck at Willis Tower, cheer for the Cubs at Wrigley Field, or sample a Chicago-style, deep-dish pizza. The city is host to an endless number of experiences that should be on every traveler’s list.
Although Chicago hotels can command a premium, you can find ways to stay affordably, even in prime neighborhoods.
Located in the central business district, the Club Quarters Hotel, Central Loop acts as the perfect base for both work and for leisure. Near Willis Tower, the Art Institute of Chicago, and other attractions not to miss, it’s also a short walk to Millennium Park, where you can catch a glimpse of the famous “Bean.”
Club Quarters, Wacker at Michigan has an enviable location on the water, not far from the Chicago Riverfront. It’s just a block from one of the most famous shopping districts in Chicago, the Magnificent Mile. Stop into a boutique to pick up a souvenir – or meander to the many nearby downtown sights, including the Institute of Contemporary Art.
1723 N Halsted Street
Grant Achatz’s multi-course menu is an immersive, interactive journey of the senses — it’s a once-in-a-lifetime experience with a price tag to match and one of the most reputable restaurants of the city’s culinary scene.
800 West Randolph Street
This dimly lit diner-style restaurant, serving roasted bone marrow and chopped chicken liver, has leather booths, dark wood paneling, and a zinc bar serving classic cocktails.
185 N. Wabash Avenue
Located in Club Quarters Hotel, Central Loop, this British pub features mini sausage rolls, fish and chips, and bangers and mash, including wallet-friendly happy hours on the weekdays.
Several locations
A family run pizzeria, with multiple locations around Chicago, Lou Malnati’s turns out a delectable deep-dish Chicago-style pizza made with generations-old recipes.
1020 W Madison Street
Peer behind the bar to get a glimpse of the kitchen crew mixing and rolling dough for the hand-crafted pastas at this Italian restaurant, which serves both traditional and modern cuisine.
Lake Street to the lakefront
This riverfront pedestrian promenade stretches just over a mile along and has a host of attractions including waterfront dining, cafes, a cocktail bar and a winery.
233 S Wacker Drive
Formerly known as the Sears Tower, this Skidmore, Owens & Merrill structure was once the world’s tallest building. Take the elevator to the sky deck on the 103rd floor, where you can take in the panoramic views and step out onto the glass-bottom Ledge, which makes you feel suspended in the air.
This urban park– one of Chicago’s many urban green spaces– is home to gardens, fountains, outdoor exhibitions as well as Anish Kapoor’s polished steel Cloud Gate. Be sure to stop by Frank Gehry’s visually stunning Jay Pritzker Pavilion, an outdoor amphitheater that looks like a tangle of twisted ribbons.
Chicago Architecture Center/Architectural Boat Tour
111 E Wacker Drive
Chicago’s marvelous architectural history is on display at this interactive museum with rotating exhibits and models of some of the city’s iconic skyscrapers. The Center is located right above the pier where passengers board the docent-led tour of the Chicago River. The architectural boat tour is one of the best ways to get panoramic views of the skyscraper-studded city—from Neo-gothic towers to curvilinear concrete structures.
1060 W Addison Street
Join cheering fans of Chicago Cubs at this ivy-covered ballpark built in 1914, the second oldest in the nation. Between innings, grab a Chicago-style hot dog to take to the stands—dressed with mustard, relish, chopped onion, sliced tomato, a pickle spear, sports peppers, and celery salt.
Michigan Avenue
Also known as Michigan Avenue, Magnificent Mile (or Mag Mile as some call it) is a mix of historic buildings, luxury shops, and department stores that draw high-end shoppers, particularly around the Oak Street District.
1512 N Wells Street
This apothecary-style shop sells spices sourced from around the globe, from barbecue rubs to signature blends.
Wooly Mammoth Antiques & Oddities
1513 W Foster Avenue
A cabinet of curiosities with maps, vintage taxidermy, skulls, and other unusual items.
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Getting Here
Chicago is served by two major airports: Chicago O’Hare (ORD) and Midway (MDW), both accessible with shuttle services to various points of the city. Amtrak trains offer nationwide service and arrive at Union Station.
Getting Around
The Chicago Transit System (CTA) has a comprehensive network of rapid-transit trains and buses. Taxis and ride shares are readily available, and a water taxi service runs along the Chicago River. The Divvy bike share program has stations around the city, with per-ride or day passes for urban cyclers.
Know the Lingo
Chi-town (pronounced SHY-town): Chicago The Bean: The Cloud Gate Sculpture The Hawk: A cold wind off of Lake Michigan The Lake: Lake Michigan The “L” : Train lines that run above the streets of Chicago, short for elevated LSD: Lake Shore Drive Out South: The South Side or south suburbs Pop: soda Sammich: Sandwich Show: The movies
Insider Tips
Chicago has many blockbuster museums, but don’t forget some of the smaller-scale gems such as the Charnley Persky House Museum and the Frank Lloyd Wright Home and Studio. The hours and tour capacities of some of these sites are limited so be sure to plan and reserve in advance.
Philadelphia
Philadelphia Visitors GuideIf you’re planning a trip to The City of Brotherly Love, we’ve created a Philadelphia visitors guide packed with plenty of things to do during your stay.
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