Don’t call it Chi-town or the Second City. Chicago, Illinois is the first in many things and rivals fellow American cities in terms of its cultural offerings and restaurants. Once home to Native American tribes and fur traders, the city’s turning point was the World’s Columbian Exposition of 1893. It took place in the wake of the Great Fire and contributed to many of the buildings you see today. Names like Frederick Law Olmsted and Frank Lloyd Wright cut their teeth in the city. These days, it’s known for Lollapalooza, one of the nation’s largest music festivals.
Many travelers never make it outside of “The Loop,” the downtown area where most attractions lie that is named for the train that loops around in a circle. But its over 70 neighborhoods are what sets Chicago apart.
River North is where I based myself during my trip, as it has a number of restaurants and shops but is well serviced by public transportation to get into the Loop and to the airport. Formerly a warehouse district, it became residential in the 1970s, centered around the Merchandise Mart.
Wrigleyville and surrounding Lakeview are most associated with being the home of the Chicago Cubs. It’s a popular spot for after work drinks or to watch sports games at dive bars. The former working class neighborhood also has rooftop bars with stadium seats.
Wicker Park and Bucktown are a popular excursion for the thriving retail and restaurant scenes. Art galleries line the streets as well as vintage shops popular with the millennial crowd. It contains its namesake park and is made up of a national historic district.
Boystown is one of the nation’s largest LGBTQ+ neighborhoods and is home to the city’s annual Pride festivities. In addition to the bars and restaurants, Boystown boasts a thriving theater and entertainment scene.
West Loop is another former industrial area turned dining hotspot. Just about every type of cuisine is represented. It’s also home to the Chicago French Market. Neighboring Greektown is home to cultural attractions.
Restaurants and Cafes
Ask a local what you should do in Chicago and they’ll likely name a number of restaurants. New York is no longer the unrivaled capital of dining, thanks to names like Rick Bayless, Stephanie Izard, and Art Smith. Grab a seat at the bar of these highly-praised restaurants or go for lunch. Chicago also boasts classic eateries that serve their signature hot dogs and deep dish pizza.
Little Goat Diner– An affordable alternative to Izard’s neighboring The Girl and the Goat, the upscale diner serves breakfast all day, burgers, and traditional dishes with a twist.
Portillo’s– Everyone has their favorite hot dog and sandwich shop and this one has locations around town. They’re also known for their spicy beef sandwiches covered in gravy.
Sunda– The Asian fusion menu at this trendy spot includes sushi, craft cocktails, and noodle dishes. I recommend the garlic butter crab noodles, which are exactly as delicious as they sound.
Seoul Taco– Originally a food truck, this restaurant now has locations around the Midwest. Try the Gogi bowl for both Mexican and Korean flavors, paired with a Jarritos soda.
Revival Food Hall– Set in a busy office building and co-working space, this food hall has burgers, tacos, poke, pizza, barbecue, and even a small book and record shop.
The Purple Pig– It can be hard to get a table at this James Beard award-winner, so go for lunch. They’re known for their cheeses and cured meats as well as internationally-inspired entrees.
Ramen-san– Belly up to the tables for a massive bowl of ramen with authentic broths and toppings. The spicy miso comes with ground pork and should always be topped with a soft boiled egg.
The Hampton Social– Their “Rose All Day” sign made them Insta-famous, but the food lives up to the hype. Brunch is the best time to visit this nautical-inspired eatery for live music.
Parson’s Chicken & Fish– Located in Logan Square, this restaurant is inspired by its surroundings. Dishes are sourced locally, including fried chicken and fish and brunch items.
For more restaurant recommendations, check out Eater Chicago.
Bars and Nightlife
The drinking scene in Chicago is diverse to say the least, from dive bars serving the Chicago staple Jepson’s Malort (don’t do it!) to swanky cocktail bars using ingredients like activated charcoal.
Three Dots and a Dash– For a taste of the South Pacific, check out this basement tiki bar. The cocktails come in quirky glasses, made with rum and fresh fruit juices.
The Signature Lounge– Instead of paying to go to the observation deck, spend the same amount of money on a drink at the 95th floor of the John Hancock Building. Try their “signature” champagne.
Broken Shaker at Freehand Chicago– The award-winning bar of the Freehand brand has an outpost in Chicago, bringing the same top notch cocktails as their Miami location.
Headquarters Beercade – River North– The sprawling beer bar features a main level with entertainment and a basement with your favorite arcade games from childhood. They have an extensive menu of craft beers from the Midwest and beyond.
Pops for Champagne– Celebrate at this champagne bar and nightclub, which has over 200 bottles of bubbly. They also have cocktails and food as well as live music many nights of the week.
Cindy’s Rooftop Bar– Located atop the Chicago Athletic Association Hotel, it’s just one of many watering holes inside the property. Their “spirits guide” crafts unique and seasonal concoctions like the Reanimator, pictured.
The Green Mill– Drink in the history at this legendary jazz club, which retains the look of the 1940s. It’s been featured in dozens of films and still hosts weekly poetry slams.
Hopewell Brewing Company– This chic brewery is one of the city’s newer ones, but already has a following for its lagers, IPAs and saisons. The taproom is the best place to see what’s new and grab a special release to take home.
Goose Island Beer Company– Easily the most well-known brewery in the region, the West Town taproom offers tastings and tours. You can also try brews that aren’t yet nationally distributed.
Revolution Brewing– The largest independently-owned brewery in the state, Revolution crafts IPAs, porters, wits, and other beers. Visitors can stop by the brewery for tours or visit the Logan Square brewpub for food and beer.
For more of Chicago’s best watering holes, follow Thrillist.
Things to Do
Willis Tower– The city’s most popular landmark, and formerly the tallest building, has some of the best views around. Grab a CityPass for shorter lines and entry into other city attractions. The John Hancock Building also has an observation deck.
The Art Institute of Chicago– It’s easy to spend hours roaming the hallways of this institution that spans the entire history of art. Don’t miss the Thorne miniatures or the impressionists.
Field Museum of Natural History– While it’s popular with field trips, this museum isn’t just for kids! Highlights include the dinosaur fossils, rare gems, Egyptian mummies, and Native American exhibits.
Wrigley Field– During baseball season, catch a game at one of the sport’s oldest stadiums. You can also take a behind-the-scenes tour, which runs throughout the year.
Museum of Contemporary Art– If the Art Institute wasn’t enough for you, this space, in a German Rationalist design, is full of pieces and exhibits on what’s happening now in art.
Navy Pier – Museum Campus– Ride the Ferris Wheel that soars above Lake Michigan. Boat and bus tours also leave from here and the space holds seasonal exhibits and experiences like ice skating.
Millennium Park– Formerly a run-down space, it’s now the city’s most popular park for its art pieces, namely the Cloud Gate (“The Bean”), the Crown Fountain (spitting faces), and the Frank Gehry-designed pavilion.
Second City– New York is known for theater, but Chicago is known for comedy. Attend one of their performances and you might just see a well-known performer or someone yet to make it big.
Chicago Cultural Center– A free museum, the cultural center is a stunning Beaux Arts space with rotating exhibits.
Frank Lloyd Wright Home and Studio– I visited the home of the famous architect in the Chicago suburbs, which is the best place to learn about the man and his work. He also has a number of designs around the city.
Shedd Aquarium– One of the nation’s leading conservation aquariums is in Chicago, dating back to 1930. Today it focuses on education, with over 30,000 animals calling it home.
Other Tours– There’s something for every interest, including the Chicago Gangster Tour, covering Al Capone and his contemporaries, Chicago Film Tour, which features Ferris Bueller’s Day Off locations, and even the Chicago Pizza Tour that takes you to the city’s best pie spots.
Pick up unique souvenirs for yourself around the city from the local boutiques, all selling the best items showcasing their city pride. But if you’re looking for retail giants, you’ll find them as well. Magnificent Mile is the most well-known shopping destination, but mostly features national stores.
Green City Market – Lincoln Park– This farmers market operates year-round, including outdoor in Lincoln Park and indoor during the winter. Here you’ll find locally made produce, cheese, prepared foods, and artisinal goods.
Eataly Chicago– While it’s not the first, Eataly Chicago has everything you love from the original, including products shipped straight from Italy as well as prepared foods and full-service restaurants.
Luxury Garage Sale– This store’s Chicago locations turn the consignment concept on its head with hand picked clothing, jewelry, and accessories. And the prices are well below retail.
Jayson Home– While they’re hard to take home as souvenirs, it’s worth driving to bring back the vintage treasures and unique furnishings from this Chicago store.
Myopic Books– Cozy up with a good read at this independent bookseller in the Wicker Park neighborhood.
For more of Chicago’s best shopping, check out Choose Chicago’s guides.
Where to Stay
There truly is something for every budget in Chicago. The Ambassador and the Drake have long been luxury staples in the city, but there’s also been a rise in boutique brands and trendy hostels.
Freehand Chicago– The rooms at this luxury hostel chain are small on space, but they make up for it with design and amenities. Beds are comfy and breakfast is free. They also have Broken Shaker, the cocktail bar, and Cafe Integral, a Nicaraguan coffee shop.
FieldHouse Jones– It’s easy to miss this River North building, but the sports-themed design hostel is worth a stay. Bunk beds are full sized as are the lockers. Community space includes a coffee shop with free coffee and pastries, a full sized kitchen, and game room.
Chicago Athletic Association– If you’re prepared to splurge, you will be glad you did. The historic landmark was once the city’s athletic club and was completely renovated, adding in sports-themed rooms, restaurants and bars, a coffee shop, and even Shake Shack that can be ordered via room service.
Wicker Park Inn– Stay where the locals live at this cozy inn. Choose from hotel-style rooms that come with breakfast or self-serviced apartments with full kitchens.
Acme Hotel Company Chicago– Another boutique spot is this trendy hotel with a restaurant and cocktail bar, bakery, and chic guest rooms.
Airbnb– Get the local experience by staying with one. There are rental options all over the city.
Most travelers arrive in Chicago via O’Hare Airport, but others come into Midway Airport. O’Hare is easily accessible to downtown via the Blue Line on the L, the name for the rail service. Midway is on the Orange Line. It takes around 45 minutes each way to get to both airports. Alternatively, you can book a private transfer from the airport to downtown Chicago or catch a cab or rideshare.
Amtrak operates out of Amtrak Station – CHI, which also where one of the Megabus stops is located. The Greyhound bus stop is to the west in Greektown. It’s easy to get around through Chicago’s public transportation system, which includes buses and the L. Purchase a Ventra card, which you can top up during your stay.
It’s also easy to walk around much of the city, but be prepared with appropriate footwear. Travel Insurance is a wise purchase, especially if you’re visiting during the winter when it’s easy to slip on ice. Chicago also has a bike share program, Divvy bikes.
Uber and Lyft both operate in the city, which is ideal for getting home at night or those early morning airport runs. Get a discount on your first Lyft ride by using the code “CAROLINE868074”.
Choose Chicago provided me with a CityPass to assist in my research. This post contains affiliate links.