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Make like Ferris and play hooky in this big city with small town charm. Home to first-rate architecture and museums, innovative restaurants (it's not all pizza and hot dogs), and comedy greats, The Second City more than makes up for its brutal weather.

Explore Chicago

542 Places
3 Itineraries
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Explore Chicago

542 Places
3 Itineraries
See all places

The city of glittering skyscrapers, Barack Obama, and the Bulls, Chicago has come a long way since its heyday as the playground for gangsters. Affectionately known as the city of neighborhoods, Chicago has 77 in all — each distinct in its own way. It's oftentimes overshadowed by its cousins on the East and West coasts, but this port city is no black sheep. It flaunts a vibrant waterfront, healthy comedy and jazz scenes, and dining that dares you to try experimental fine dining and cheap eats alike. Even with a blistering winter, Chicago has so much to offer — and its Midwestern friendliness will make you feel right at home.

About Chicago

(Photo Courtesy: iStock/JaySi)

When to go:

Winters in the Midwest are no laughing matter. Because of the lake-effect phenomenon off Lake Michigan, Chicago winters are especially blustery and snowy, with temperatures dipping well below freezing. It may be an unpopular time to visit but that means less tourists and better deals. If you visit between December and late March, invest in good winter clothes, bundle up and plan for activities indoors.

(Photo Courtesy: iStock/Ryszard_Kania)

Spring means warmer weather but it also means unpredictability: you may encounter winter conditions well into April so have a decent jacket on hand. Once the frost thaws, moderate temperatures (between high-50s and low-70s) make it pleasant for walking around. May and June tend to be rainy months and summers can be hot and muggy (mid-80s), but in general this is when Chicago is at its best. Sit lake-side and take it all in at places like the Navy Piers or any of the numerous festivals going on around town at this time. Fall weather is also unpredictable but it stays relatively warm (between the 60s and 70s) and usually it doesn't rain; you can enjoy many of the popular summer outdoor activities well into October before the temperature begins to drop into the 40s.

Getting around:

(Photo Courtesy: iStock/Mlenny)

The elevated train, known as the "L" (though not all eight of them are elevated), is the second busiest rail mass transit system in the United States after New York. They connect to subway and street-level trains and serve over 140 stations across the city. The Blue (airport and downtown) and Red (connecting the North and South Sides) lines operate 24 hours a day, but all other trains stop services at varying times. Some lines start service as early as 3:30am and can run as late as 2:20am, but it's a good idea to check exact times before heading out.

The bus network is also expansive and can take customers between downtown and the North and South Sides. Again, all bus lines operate on different schedules; some can run as early as 4am and as late as 11pm, while other lines provide owl (24-hour) services. Schedules are available and updated daily for all bus lines.

Single-ride fares are $2.50 for "L" trains and $2.25 for buses. You can buy disposable paper single-ride and 1-day tickets at vending machines (located in every "L" station) or purchase a reusable Ventra card (tap-and-go) at vending machines or participating retail locations. New Ventra cards cost $5 and can be used on trains and buses. Note that cash is only accepted on buses and at vending machines to add value to Ventra cards. Day passes are available for purchase for those who will be relying on the transit system during the duration of their trip: a 1-day CTA pass costs $10, a 3-day pass for $20, and a 7-day pass for $28. Rides to and from O'Hare International Airport are $5 through Ventra cards or pay-as-you-go.

In nice weather, you may consider taking Chicago by foot. The downtown grid is easy to navigate and many major attractions are located within walking distance of each other. Major ride hailing services like Uber and Lyft are popular and readily available, and are a great option if you plan to be out after "L" train service ends. As always, they provide a fixed price depending on distance and demand. Renting a car, on the other hand, is not recommended as traffic gridlocks occur often around the city, especially in the downtown area, and street parking is difficult.

Talk money to me:

US dollars is the official currency. Major credit cards are accepted almost everywhere but it's not a bad idea to keep some bills on hand for small transactions and for picking up the tab at the rare cash-only establishment.

Let's talk about food & drinks:

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Forget your presumptions about Midwestern cuisine (see: meat and potatoes). As the third largest city in the country, Chicago's food options are infinite and well-respected by industry bigwigs. Case in point: the esteemed James Beard Foundation awards, which presents accolades to influential figures in the culinary industry, relocated to Chicago until 2021. When it isn't busy serving as a base for the top food experts in the world, the city hosts some of the finest fine dining (and cheapest cheap eating) establishments in the country.

Chicago is a big steakhouse city (after all, it is the meatpacking capital of the world), but you'll probably want to skip any stuffy, wood paneling setting and go straight for the burger at Au Cheval (who some claim is the best burger money can buy). Recently, molecular gastronomy has set roots in Chicago as well. Celebrated chef Grant Achatz helms the creations at Alinea, where visitors can partake in dishes that are as much science experiments as they are a dinner for two.

When it comes to pizza, even out-of-towners know that deep-dish pizza reigns supreme here —and there's plenty to choose from. You can't go wrong with heavy hitters like Pequod's or Giordano's. But believe it or not, deep-dish isn't the go-to for locals; thin-crust is. Pizza cut into squares, or tavern style, with a thin-crust outsells deep-dish by a long run. Bite into a world-changing square with toppings at Vito & Nick's, even if you have to travel close to an hour to South Side. Of course, regular slices exist in Chicago too, but you won't be chastised for not folding it in half like they do in New York. Just an FYI: pepperoni may be America's favorite pizza topping, but in Chicago it's all about the sausage.

Hot dogs are another dish synonymous with Chicago — but think twice before squeezing ketchup on that wiener (that's a no-go around here). Instead of the popular condiment, Chicago style dogs come topped with yellow mustard, bright green relish, chopped white onions, tomato slices, a dill pickle spear, pickled sport pepper, and celery salt, all served on a poppy seed bun. Try it all at Wiener's Circle (if you can stomach the entertainment), Portillo's, or the aptly named Dog House in Lincoln Park.

(Photo Courtesy: iStock/bhofack2)

And then there's the Italian beef sandwich, the cousin of the Philly cheesesteak but without the cheese. The story goes that the sandwich was born here after World War I when a street peddler attended a traditional Italian peanut wedding. The thin beef slices are cooked in their own juices (or "gravy") and served on an Italian-style roll. For toppings choose between giardiniera peppers (known as "hot") or sautéed green Italian sweet peppers (known as "sweet"). First time visitors should start their Italian beef sandwich adventures at celebrated Al's Beef.

When it comes to Mexican food, don't think you're out of luck just because you're not in Southern California. In the early 20th century, thousands of Mexican immigrants flocked to the Second City to work in steel mills, meatpacking houses, and factories. The community grew so large that by 1929, Chicago was the second largest outpost for Mexican emigrants outside the Southwest. The diversity in regional Mexican cuisines is represented best in the neighborhoods like Pilsen and Little Village. Dishes like mole or a spicy beef tripe soup known as menudo see varying interpretations from one restaurant to the next. Swing by Taqueria Los Comales in Pilsen as early as 8am for a sope, or opt for multi-regional small plates (or one of three tacos) at Mi Tocaya.

There's no better way to wash it all down than with a beer in hand, and luckily, you're in the right place for it. As of 2018, Chicago became the home of the most breweries in any city in the nation (there are currently over 160). While there is no one cause for this sudden influx, it's safe to say Chicagoans love their beer. Lost on where to begin? Our guide to the craft beer scene in Chicago is yours for the taking.

Good to know:

(Photo Courtesy: iStock/Mlenny)

  • Chicago did not earn its nickname because of the wind gusts coming off Lake Michigan. According to local legends, Chicago is windy because of the bloviating politicians in town who were "full of hot air."
  • Never call it Chi-Town, unless you're being ironic (but even then, don't).
  • Geographically speaking, everything below I-290, or the Loop, is considered the South Side, and everything above is considered the North Side. While the North sees more hype, the South is where a majority of the city's population lives.
  • While jazz may be conflated with New York and the Harlem Renaissance, the term jazz was actually coined in Chicago in 1914.
  • The Chicago River flows backwards away from Lake Michigan, which is the city's main water supply. Canals were built to reverse the river's flow toward the Mississippi River and Gulf of Mexico, seeing completion in 1900.
  • If you think you smell chocolate in the air, you're not incorrect (or crazy). The Blommer Chocolate Factory is located in West Loop and if you're walking nearby, you'll likely be treated to delicious smells of chocolate. The smell is so prevalent that a local Chicagoan started a blog that mapped the smell across the city each day.
  • Generally, bars stay open until 2am, which means last call is around 1:30am. But there are many locations around the city that remain open until 4am or later at least once a week, meaning last call is around 3:30am.
  • Smoking and the use of e-cigarettes is prohibited in enclosed public places and 15 feet of entrances and exits.
  • Chicagoans happen to be friendly, but they're also really funny. The Second City Club, which opened in 1959, is one of the biggest names in comedy and improv in the world. The likes of Tina Fey, Steve Carell, and John Candy had their breakthroughs here.

(Photo Courtesy: iStock/smontgom65)

  • Since baseball runs through the veins of all Chicagoans, it's important to know which team to root for — and it all comes down to geography. The Chicago Cubs play at Wrigley Field (the second-oldest active major league ballpark in America) in the North Side and the White Sox play at Guaranteed Rate Field in South Side. If you want to sound like a local, or baseball fan, the rivalry is also known as the Windy City Showdown, among other names.
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Major Neighborhoods

Chicago is a city of neighborhoods — there are 77 in total, making it impossible to visit them on your first trip. Below are a few highlights and not-to-miss areas:

For the best museums:

(Photo Courtesy: iStock/smontgom65)

You'll discover some of Chicago's top museums in and along Grant Park in the Loop and Near South Side districts. Marvel at Edward Hopper's Nitehawks at the The Art Institute of Chicago or analog and digital creations at the Museum of Contemporary Photography. The Field Museum of Natural History in particular is a favorite among locals and visitors; it is home to over 20 million objects and Sue, the largest and most complete T.Rex ever found. Around 1,500 of the artifacts here are available to rent thanks to the N.W Harris Learning Collection. The Adler Planetarium will take you to the far flung reaches of the cosmos and if you emerge from the Grainger Sky Theater near sundown, you'll be treated to a spectacular view of the skyline at night.

Just across the river in the Streeterville neighborhood is the Museum of Contemporary Art which houses one of the largest contemporary art collections in the world. Kids can go on a dinosaur dig at the Chicago Children's Museum before hopping on a Ferris wheel ride at the Navy Piers. The Museum of Broadcast Communications in River North allows visitors to trace the history of communications before presidents could take to Twitter. Or pop by Pilsen where you'll be treated to some of the city's most colorful murals, leading contemporary art galleries, and a museum celebrating the neighborhood's predominantly Mexican-American culture.

For the best shopping:

(Photo Courtesy: iStock/stevegeer)

Wicker Park and Bucktown are a treasure trove of trendy boutiques and one-of-a-kind gifts. Penelope's carries European labels (think A.P.C.) and stylish home goods; boho enthusiasts need go no further than Moon Voyage for statement jewelry and apothecary necessities, not to mention chic designs from abroad; and high-end streetwear hypebeasts can seek fashion therapy at RSVP Gallery, which stocks up everything from 3.1 Philip Lim to Acne Studio designs. Eskell or Stitch can help turn your apartment into an Instagram decor sensation, while Vintage Underground will cure your hankering for timeless pieces. Male shoppers looking to turn heads — or simply in need of decent outerwear and a game of pool — take Stock Mfg. Co. in Near West Side into consideration.

Shops in Lincoln Park are housed inside charming Victorian rows and brownstones, like Elizabeth Grace, where you'll find a great selection of all things stationery. Cosmetic junkies can rely on Credo Beauty for wellness products; and bookworms take solace in the used, rare, and out-of-print bookshop, Myopic Books.

For a slice of nightlife:

(Photo Courtesy: iStock/Sean Pavone)

The Loop, although the center hub for Chicago, tends to get pretty dead after the work day. If nightlife is a priority for you, opt instead for nearby River North. The area is packed with a standout roster of dining options including chef Ricky Bayless's Frontera Grill. Wicker Park and Bucktown though, are really where it's at. The two neighborhoods contain everything. There are chic cocktail bars and arcade bars, watering holes with local talents, and cozy dive bars to knock back a few. The demographic of these neighborhoods skews young, so expect bars to stay open late with lots of trendy types getting their buzz on.

Logan Square has its fair share of fancy restaurants and bars, but when the night hits, so do the parties. Dance to a DJ set at places like Slippery Slope, where concertgoers and late-night shift workers come ready to let loose. Also, here's your chance to try one of the countless breweries in town. Things take a glitzy turn at West Loop where happy hours hit new heights — literally. Choose from three bars inside Mexican restaurant La Josie, one of which is located conveniently on the rooftop; sip expertly made drinks at Cindy's, located on the rooftop of the Chicago Athletic Association Hotel; or, if you prefer things closer to the ground, the Aviary's inventive cocktails will make you soar.

Cubs fans don't need to settle for overpriced beers at Wrigley Field. Post-baseball drink options abound in Wrigleyville and adjacent Lake View and Roscoe Village. Sip your favorite craft beers in a garden, risk brain freeze with the alcoholic slushies at a famed gay club, or save money on tickets and cheer for the Cubs at this historic sports bar instead.

For nature lovers:

(Photo Courtesy: iStock/franckreporter)

Although Chicago is known for its blistering winters, the city has 25 beaches running along the 26 mile shoreline of Lake Michigan that you can take advantage of during the summer. Water temperatures average a refreshing 75 degrees, while closer to shore you'll find waters around 80 degrees or higher. Check temperatures before taking the plunge.

You don't have to travel very far to see some greenery thanks to the city's urban parks. Grant Park stretches over 300 acres along Lake Michigan and offers a lakefront trail, rock climbing, tennis courts, and a skatepark. Not to mention, some of the most recognizable sights of the city are nestled here. Millennium Park attracts locals and tourists to its cultural and art events, picturesque promenades, theaters, Crown Fountain, and most notably, Cloud Gate, the reflective steel structure affectionately known as "The Bean." Other pockets of green space exists throughout, including North Park Village Nature Center, the Alfred Caldwell Lily Pond north in Lincoln Park (and just north of the Lincoln Park Zoo), or Garfield Park which boasts and impressive conservatory — one of the largest in the country.

For older couples:

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The scholarly Hyde Park will suit those looking to slow down the pace. The lovely neighborhood hosted the World Fair in 1893, where the Ferris wheel and electricity were introduced to the world. Today it is surrounded by cultural institutions: the scenic University of Chicago, the DuSable Museum of African American Art, and the Museum of Science and Industry. Fans of Frank Lloyd Wright can find his work all over the city (including his own home and studio). The Frederick C. Robie House in Hyde Park is one of Wright's best known examples of Prairie design. Keep in mind that former president Barack Obama lives in the area so you may notice a few Secret Service agents roaming the streets. Hotspots like The Promontory will get your appetite and heart going to the live music, whereas the Garden of the Phoenix in Jackson Park will have you zen all over again. In September, catch jazz's latest stars during the Hyde Park Jazz Festival.

Magnificent Mile feeds into the affluent neighborhood of Gold Coast, whose proximity to downtown makes it convenient for visitors who want the best of both worlds. You'll find chic bistros, brasseries and classic Chicago steakhouses next to luxury boutiques and designer studios peppered throughout. It is a very happening and pedestrian-friendly part of town. But Gold Coast also offers a reprieve from the traffic and bustling city noises with its historic 19th- and 20th-century mansions, mostly residential streets, and superior lakefront access. Fun fact: the original Playboy mansion, now a landmarked building, is located in Gold Coast.

For families:

Staying in and around The Loop is a great way for families to experience Chicago to the fullest. Whizz between skyscrapers as you ride on the "L" train or take the kids on a riverwalk. That being said, be warned: The Loop shuts down after work hours so if you're a parent looking for nightlife after the kids have gone to bed, you likely won't find it here. Alternatively, try River North for some of the city's most iconic shops and for strolling along Magnificent Mile. Don't forget to visit the Chicago Children's Museum and the Shedd Aquarium in Grant Park. Catch a glimpse of lions, tigers, and bears at Lincoln Park's Lincoln Park Zoo (it's free!), enjoy 1,200 acres of greenery at Lincoln Park, or on warm days, take to North Avenue Beach, one of Chicago's most popular.

For the Swedish and LGBTQ communities:

(Photo Courtesy: iStock/stevegeer)

The largest LGBTQ community calls Andersonville home, as did thousands of Swedish immigrants who flocked to the area as early as the 19th-century. The neighborhood is anchored by the Swedish American Museum (identifiable from the water tower painted with the Swedish flag) and a charming collection of mostly independently-owned shops. Whether you're here to eat a smörgåstårta (a savory cake with many fillings and garnishes), to celebrate Pride or to get your hands on a burger at popular the popular Hamburger Mary's, Andersonville has enough of that old-school meets quirky neighborhood vibe you've always dreamed of.

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Chicago's must-visit places

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