Waldorf Astoria

Address: 11 E Walton Street
Phone: (312) 646-1300
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If you’re looking for luxury, the Waldorf Astoria in Chicago is a great place to find it. This 60-story hotel and condo tower is just 10 years old and located in the heart of Chicago’s Gold Coast. It’s designed as an homage to the grand hotels of 1920s Paris, complete with colonnades, a cobblestone courtyard and impeccable service. Rooms are spacious and bathrooms are perfect for lounging in a bathtub full of bubbles.

The Drake Hotel

Address: 140 E Walton Place
Phone: (312) 787-2200
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The Drake Hotel is a luxurious historic landmark at the top of the Magnificent Mile just a couple of blocks from the 360 Chicago and just one block south of Oak Street Beach. The hotel opened in 1920 and over the years has welcomed guests including Prince Charles and Princess Diana, Elizabeth Taylor, Judy Garland, Winston Churchill, Herbert Hoover, and Walt Diskey. Joe DiMaggio and Marilyn Monroe carved their initials into the wood bar of the hotel’s Cape Cod Room, and those initials are still there today.

The Langham

Address: 330 North Wabash Avenue
Phone: 312-923-9988
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This luxury hotel is housed within architect Mies van der Rohe’s last skyscraper. The hotel occupies the building’s first 13 floors, and offers some of the best bathtub views in Chicago. It is located along the Chicago River just a block from the shops of Michigan Avenue. Its Pavilion Lounge is known for its afternoon tea, and the hotel itself is something of a museum and houses 150 pieces of art.

The Peninsula

Address: 108 E. Superior St.
Phone: (312) 337-2888
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If you’re looking for a larger than average hotel room, The Peninsula is the hotel for you. The decor is inspired by Lake Michigan, and the in-room tech addresses every need you could have. Pets are welcome for a bargain $50 a night, and the hotel lobby is far more than what it might seem. It’s also a Michelin-starred restaurant. The hotel has a rooftop pool for swimming with a view.

St. Regis Chicago

Address: 401 E Wacker Drive
Phone: (312) 787-3447
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Chicago’s former Vista Tower is now rebranded as The St. Regis Chicago. It sits in the Lakeshore East neighborhood, a couple of blocks from the iconic Millennium Park. The hotel offers classic St. Regis amenities like butler service and afternoon tea. But the most notable feature is its wellness floor, which has a gym with river views, a 12,000-square-foot spa, an outdoor sundeck, and a heated indoor swimming pool with views of Lake Michigan. The hotel has 192 suites, but T+L’s news director Paul Brady said the presidential suite is especially memorable for its lake-view soaking tub. “Ensconced in this vertical jewel box, it’s easy to feel as if you’re the only guest in town, but the buzz of Michigan Avenue is just a few short blocks west, with the hum of the whole city beyond,” said Brady.

The Palmer House Hilton

Address: 17 East Monroe Street
Phone: (312) 726-7500
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With more than 1,600 rooms, The Palmer House is Chicago’s second largest hotel. This is a luxury hotel with history. Frank Sinatra used to perform here, and former President Bill Clinton has stayed here. The current building is the third iteration of the hotel. The first structure burned down during the fire of 1871. The second was visited by Mark Twain, Oscar Wilde, Grover Cleveland and Ulysses S. Grant. A meeting at that hotel is what gave way to the creation of the Big Ten Conference. A dressing area where performers used to prepare is still intact and hidden behind a door in the hotel’s ballroom.

The Chicago Hotel Collection – Wrigleyville

Address: 3475 N Clark Street
Phone: (773) 248-9001
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If you love baseball, this hotel was made for you. An intimate hotel with just 21 rooms, it’s a 10-minute walk from Wrigley Field. Rooms and common areas are baseball themed. The lobby has baseball bats on the ceiling, and you’ll find plenty of stadium signs all around.

The Robey Hotel

Address: 2018 W North Avenue
Phone: (872) 315-3050
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You’ll find The Robey Hotel inside a 203-foot-tall art deco masterpiece in Wicker Park. The building was designed in 1929 as an office building and has since been converted into an 89-room hotel. The hotel is just a few steps from the train to O’Hare International Airport. It has a rooftop cocktail bar with exclusive guest happy hours and epic views of the Chicago skyline. The Robey offers free bike rentals and stocks rooms with local beers.

ACME Hotel

Address: 15 E Ohio Street

Phone: (312) 894-0800

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The ACME hotel in Chicago’s River North neighborhood describes itself as a “lifestyle boutique hotel alternative for the tragically hip.” The ACME Hotel is located in a former motel that’s been gutted and turned into a trendy boutique hotel. Rooms are small but comfortable, but you may want to head straight to the basement after you check in. That’s where you’ll find the Bunny Slope, likely Chicago’s only hot tub bar.

Best Restaurants

Au Cheval

Address: 800 W Randolph Street
Phone: (312) 929-4580
Website

Au Cheval is no ordinary diner. Menu items include chicken liver, roasted marrow bones, and a signature cheeseburger like none other. The Au Cheval burger is simple: prime beef formed into four-ounce patties and layered with Kraft American cheese. It’s topped with homemade pickles and Dijonnaise, with options to add a fried egg or thick-cut peppered bacon or foie gras.

Girl and the Goat

Address: 809 W Randolph Street
Phone: (312) 492-6262
Website

Girl and the Goat is the brainchild of chef Stephanie Izard, the first female chef ever to win Bravo’s Top Chef. Izard is a James Beard Award-winning chef and has beaten chefs including Bobby Flay in cooking competitions. Girl and the Goat features family-style dishes with Meditteranean inspiration. Menu items include swiss chard-kale pierogis, grilled pork belly, wood oven-roasted pig face and goat liver mousse. Don’t skip the handcrafted cocktails or the bourbon ice cream dessert.

Gene and Georgetti’s

Address: 500 N Franklin Street
Phone: (312) 527-3718
Website

If you’re after a steak in Chicago, this is where to get it. Gene & Georgetti was founded by a pair of Italian immigrants in 1941 and is one of Chicago’s oldest steakhouses. Frank Sinatra, Bob Hope, Lucille Ball, Keanu Reeves, and Will Ferrell are among the celebrities that have dined on its giant portions of steaks, chops, and classic Italian entrees like Chicken Marsala, Eggplant Parmesan, and Veal Scaloppine.

Quartino Ristorante

Address: 626 N State Street
Phone: (312) 698-5000
Website

This is the place to go for a family-style Italian meal in downtown Chicago or a takeout meal you won’t forget. Don’t miss the eggplant parmesan, roasted baby octopus, organic veal skirt steak, or the burrata.

Joy Yee’s Noodle Shop

Address: 2139 S China Place
Phone: (312) 328-0001
Website

Joy Yee’s Noodle Shop has perhaps the most expansive menu of noodles in Chicago. The restaurant has three locations, one in Chicago’s Chinatown and two suburban outposts in Evanston and Naperville. Joy Yee’s was among the first places in Chicago where patrons could get Taiwanese-style bubble tee.

Frontera Grill

Address: 445 N Clark Street, Chicago, IL 60654
Phone: (312) 661-1434
Website

Frontera Grill was opened in 1987 by celebrity chef Rick Bayless and is widely considered one of the best Mexican restaurants in the city. Tortillas are made with organic corn from Mexico, fish is sourced from sustainable fisheries, and season vegetables dominate the menu. Frontera Grill won a prestigious James Beard award in 2007.

Giordano’s

Address: 223 W Jackson Boulevard, Chicago, IL 60606
Phone: (312) 583-9400
Website

You can’t go to Chicago and not eat a deep dish pizza. Giordano’s is one of several pizzerias serving up the local delicacy and has 65 locations spread across the country, but the one in central Chicago is the easiest to access. The restaurant traces its roots to a small northern Italian town where Mama Giordano made a popular Italian Easter Pie, the precursor to Giordano’s modern deep dish.

Lou Malnati’s

Multiple locations
Website

Lou Malnati worked at Chicago’s first deep dish pizzeria in the 1940s then made his way to the suburbs to open a pizzeria of his own. Lou Malnati’s deep dish pizzas are made from scratch using hand-selected California vine-ripened tomatoes. Mozzarella is sourced from a small Wisconsin dairy farm that’s been supplying the restaurant for more than 40 years, and sausage is flavored with an exclusive — and secret — blend of spices.

Gino’s East

Address: 162 E Superior Street
Phone: (312) 266-3337
Website

Gino’s East is the brainchild of two taxi drivers and another friend. The trio opened their first pizzeria in 1966 and have since expanded to include locations across the Chicagoland area and Texas. Gino’s East cooks their deep dish pizza with a cornmeal-like crust and the cheese on the bottom. Toppings are placed on top of the cheese, then covered in sauce.

Alinea

Address: 1723 N Halsted Street
Phone: (312) 867-0110
Website

Alinea is a three-star Michelin restaurant that’s become regular on lists of the world’s best restaurants. Chef Grant Achatz is best known for his outlandish dishes that marry creativity with phenomenal flavor. A favorite dish: an edible helium balloon made from taffy.

Tzuco

Address: 720 N State Street
Phone: (312) 374-8995
Website

The French-Mexican fusion restaurant is from Michelin-starred chef Carlos Gaytan, who began his career as a 20-year-old immigrant dishwasher before becoming the first Mexican chef to earn a Michelin star in 2013. Tzuco is meant to tell the story of Gaytan’s life through a series of unique dishes in a warm, welcoming space in Gold Coast. Dishes are meant for sharing, and you won’t want to miss the spicy roasted octopus, the barbacoa, or the traditional French onion soup with a poblano pepper twist.

Billy Goat Tavern

Address: 1535 W Madison Street
Phone: (312) 733-9132
Website

The Billy Goat Tavern is a Chicago institution that was established in 1934. It’s founder, Greek immigrant William Sianis bought his tavern, then called the Lincoln Tavern, with a $205 check that bounced. At Sianis told it, a goat fell off of a passing truck and wandered inside, inspiring him to change the tavern’s name. Billy Goat Tavern has a simple, straightforward menu that includes the Cheezeborgers made famous by “Saturday Night Live”.

Things to Do

Chicago Architecture Foundation River Cruise

Address: 112 East Wacker Dr.
Phone Number: 312-332-2505
Website

There’s nothing like seeing Chicago from the water. The Architecture Foundation’s boat tour offers an opportunity to do that while learning about Chicago architecture. The 1.5-hour cruise along the Chicago River passes the Merchandise Mart, a structure so big it has its own zip code; Marina City, a pair of residential towers known colloquially known as the corncobs, the Chicago Mercantile Exchange and Willis Tower.

Willis Tower

Address: 233 South Wacker Drive
Phone: (312) 875-0066
Website

Willis Tower, previously known as Sears Tower, is a 110-story skyscraper that was the tallest building in the world for almost 25 years. It’s now the second-tallest building in the U.S. behind One World Trade Center in New York. More than 1 million people visit the Willis Tower’s observation deck each year, making it one of Chicago’s most popular tourist destinations. The Willis Tower observation deck is located on the 103d floor of the building and now includes retractable glass boxes that extend four feet over the street below. On a clear day, visitors can see Michigan and Wisconsin.

360 Chicago

Address: 875 North Michigan Avenue
Phone: (888) 875-8439
Website

The John Hancock Building’s 360 Chicago observation deck is located 1,000 feet above the Magnificent Mile and offers 360-degree views of the Chicago skyline and Lake Michigan. Up for adventure? Try the enclosed moving platform that tilts visitors over Michigan avenue. You don’t have to head to the observation deck to check out the epic views though. Just take a trip up to the Signature Room restaurant and bar to take in the Hancock Tower’s lake and city views over cocktails or a buffet brunch.

Go to the beach

Multiple locations
Website

Believe it or not, Chicago is a beach town where you can bask in the shadows of skyscrapers while digging your toes into the sand. Chicago has 26 miles of lakeshore and 25 beaches. North Avenue Beach, just north of downtown, is popular for yoga and beach volleyball. Oak Street Beach is closest to downtown Chicago. Admission to Chicago’s beaches is free. Lifeguards are on duty between 11 am and 7 pm during the summer.

Art Institute of Chicago

Address: 111 S Michigan Avenue
Phone: (312) 443-3600
Website

The Art Institute of Chicago is one of the oldest and largest art museums in the U.S. More than 1.5 million visitors pass through its doors each year to see a collection that includes Picasso’s The Old Guitarist, Edward Hopper’s Nighthawks, and Grant Wood’s American Gothic. The museum spans almost one million square feet and is housed in a gorgeous beaux-arts building that was designed for the World’s Columbian Exposition in 1893.

Frank Lloyd Wright houses

Multiple locations
Website

Famed architect Frank Lloyd Wright came to Chicago in search of work in 1887. Throughout his career, Wright designed more than 1,000 structures, several of which are located in the Chicago area. Two good options for architecture buffs that are easily reachable by public transit are the Robie House at the University of Chicago and the Frank Lloyd Wright Home and Studio in suburban Oak Park.

See jazz at the Green Mill

Address: 4802 N. Broadway Avenue
Phone: 773-878-5552
Website

The Green Mill opened in 1907 as Pop Morse’s Roadhouse. Al Capone was once a regular and his favorite booth is still standing. The booth has views of both the front and back entrances, something important to Capone and his associates, who also are said to have used a network of tunnels under the bar to evade authorities. The Green Mill has appeared in several movies, including “High Fidelity”, “Prelude to a Kiss”, and “Soul Food”.

Field Museum

Address: 1400 S Lake Shore Drive
Phone: (312) 922-9410
Website

The Field Museum is one of the world’s largest natural history museums. Around two million people visit each year to explore its fossils, ancient cultures, and to meet Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered. Soldier Field, home of the Chicago Bears, is located across from the Field Museum.

The Second City

Multiple locations
Website

Chicago is a comedy mecca. Several of America’s top comedians got their start at The Second City comedy club, among them: John Candy, John and Jim Belushi, Joan Rivers, Bill Murray, Amy Poehler and Stephen Colbert. The Second City is one of many Chicago comedy clubs.

Stroll Through Grant Park

Address: 337 E Randolph Street
Website

Grant Park is a 319-acre urban park situated along Lake Michigan in downtown Chicago. The park is often called “Chicago’s front yard” and includes the Art Institute of Chicago, Millennium Park, and the iconic Buckingham Fountain, which was featured in the title sequence of the TV show “Married… with Children” and the movie “National Lampoon’s Vacation”. The fountain operates from 8 a.m. to 11 p.m. from mid-April to mic-October. Water shows are scheduled for every hour on the hour. Millennium Park, known for its summer concerts and winter ice skating, is located within Grant Park.

Museum of Science and Industry

Address: 5700 S Lake Shore Drive
Phone: (773) 684-9844
Website

The Museum of Science and History is located in Chicago’s Hyde Park in a building that was part of the 1893 World’s Columbian Exposition. The museum’s exhibits include a full-size replica coal mine, a German submarine captured during World War II, a 3,500-square-foot model railroad, World War II airplanes, the command module from Apollo 8, and the world’s first diesel-powered streamlined stainless-steel train, the Pioneer Zephyr. The Museum of Science and History is known for its interactive exhibits and has more than 2,000 pieces in its collection, some of which require an additional fee.

Cloud Gate

Address: 201 E Randolph Street in Millennium Park
Website

People call it the bean, but look closely at the public sculpture that sits on the edge of Millennium Park and you may see the cloud it was intended to be. Cloud Gate was designed by Indian-born British artist Sir Anish Kapoor and constructed between 2004 and 2006. It’s made of 168 pieces of stainless steel plates and has been welded in such a way that there are no visible seams.

Chicago Theater

Address: 175 N State Street
Phone: (312) 462-6300
Website

The Chicago Theater is a landmark that was built in 1921 and previously served as one of the city’s premier movie theaters. Nowadays, it hosts concerts, plays, touring Broadway shows, comedy, and more. The theater’s famous marquee is frequently used in movies, TV and artwork depicting the city. Can’t work a live performance into your Chicago itinerary? Tours of the property are available.

Best Shopping

Water Tower Place

Address: 835 N. Michigan Avenue
Phone: (312) 440-3580
Website

Water Tower Place sits at the northern tip of the Magnificent Mile and was one of the first vertical malls in the world. It offers 758,000 square feet of shopping in the heart of downtown Chicago. The mall covers eight levels and has more than 100 stores, including a flagship American Girl store, a Chicago Cubs Clubhouse Shop and mall staples like Victoria’s Secret, Sephora, Lego and Banana Republic. Located on North Michigan Avenue along the Magnificent Mile, the mall is named after the Chicago Water Tower, one of the few structures that survived the 1871 fire that devastated the city.

Oak Street

Website

If you’re looking to drop some serious cash, Oak Street in Chicago’s Gold Coast neighborhood is where you’ll want to go. This shopping district sandwiched between Michigan Avenue and Rush Street is small but packs a high-end punch with retailers like Prada, Hermès, Tory Burch, Armani, and Jimmy Choo. It’s also where you’ll find Barney’s, Harry Winston, and a Vera Wang bridal salon.

State Street

State Street is a place to find retailers including Sephora, Forever 21 and Urban Outfitters as well as the world’s second largest department store — a former Marshall Field’s that’s now a Macy’s. The 7th floor of Macy’s houses a collection of restaurants from celebrity chefs including Rick Bayless and Takashi Yagihashi.

Kokorokoko Vintage

Address: 1323 North Milwaukee Avenue
Website

If you’re a child of the 80s or 90s, you’re going to love exploring this quirky boutique. The store opened in 2009 with the goal of bringing shoppers vintage finds from the post hip-hop, pre-Internet era. Expect to find lots of T-shirts, bright prints, 80s prom dresses, and things like “90210” trading cards.

Fashion Outlets of Chicago

Address: 5220 Fashion Outlets Way, Rosemont, IL 60018
Website

If you’re looking for a deal, head to the suburb of Rosemont where you’ll find retailers including Neiman Marcus Last Call, Nordstrom Rack, Gucci, and Saks Fifth Avenue’s Off 5th of Rosemont where you’ll find the Fashion Outlets of Chicago. It’s only a half-mile from Chicago O’Hare International Airport, making it perfect for a long layover shopping spree.

Wicker Park

Website

If you’re a vintage shopper, head to Wicker Park where North Avenue meets N Milwaukee Avenue. Walk southeast on Milwaukee and you’ll find a number of vintage retailers including Buffalo Exchange, Ragstock, Una Mae’s, and Vintage Underground.

Lincoln Park

Website

Lincoln Park is a boutique shopper’s paradise where you’ll find one-of-a-kind retailers selling clothes, gifts, furniture and more. Among some of Lincoln Park’s more popular shops: Alice & Wonder, Enzo Custom and Art Effect. Lincoln Park is also home to several chain retailers and the world’s largest Lululemon.

Open Books

Address: 651 W. Lake Street
Phone: 312-475-1355
Website

Open Books is a nonprofit used bookstore that aims to boost literacy in Chicago. Open Books runs a number of programs for students and provides free books to schools, libraries and nonprofits across Chicago. It has two locations, one in the West Loop and another in Pilsen. The West Loop location alone has more than 50,000 books in its inventory. It’s also got plenty of places to read.