Chicago [Best Bets 2026]

arts & culture | a culinary capital | festivals & entertainment | great outdoors

Chicago

C hicago is a place that truly needs no introduction. Mere mention of "The Windy City" likely conjures up many images of its famed features. The Willis (formerly Sears) Tower skyscraper; the iconic Cloud Gate (or "The Bean") in Millennium Park; historic Wrigley Field; a slice of Chicago deep dish pizza; sweeping Lake Michigan views; and a picture-perfect river running through downtown's renowned architecture. While these are all worthwhile stops, they barely scratch the surface of Chicago's 77 diverse neighborhoods. And with the ever-evolving nature of the city, a return visit to a familiar neighborhood will feel like a brand-new experience. But as the city develops, new restaurants pop up and shows roll through town, some things stay constant. Chicagoans' resilient work ethic and creative spirit. A blend of down-to-Earth Midwestern sensibility with diverse, global perspectives. And a united stance against ketchup on hot dogs.

Former President Barack Obama lived and worked in Chicago’s South Side for more than 20 years before he moved into the White House. So, when it was time to choose a location for his presidential library—a tradition that dates back to 1941 when President Franklin D. Roosevelt opened his to the public— President Obama chose Jackson Park, a waterfront park originally designed by Frederick Law Olmsted for the 1893 World's Fair in Chicago. The Obama Presidential Center is set to open in 2026. A first of its kind, the Barack Obama Presidential Library will be an all-digital presidential library, with the National Archives and Records Administration preserving physical records elsewhere. The center itself will span 19 acres, and in addition to a museum, will offer community-focused features like a garden and an events facility. It will also house a branch of the Chicago Public Library. Stay tuned for more details on the opening date.

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Rendering of the Obama Presidential Center

Arts & culture

A culinary capital

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Plan your trip

Lincoln Park

Cloud Gate in Millennium Park

River cruise

Public art in Pilsen

"Nighthawks" at the Art Institute of Chicago

National Museum of Mexican Art

French toast at Lula Cafe

Lou Malnati's deep dish pizza

Wrigley Field | credit: Heather Maguire

Music Box Theatre

Green Mill

The 606

Chicago Riverwalk

Skateboarder on the Lakefront Trail

The 606

The Center will feel at home in a city of dozens of museums, showcasing art, architecture, culture, history, science and more. Some are quite particular, like the International Museum of Surgical Science; or the Money Museum, where you take a photo in front of a million bucks. And some are expansive and world renowned, like the Art Institute of Chicago, where you could spend days wandering the halls that feature works by famed artists like Van Gogh and Renoir. And while you’ve likely heard of top attractions like the Shedd Aquarium and the Field Museum of Natural History, the intimate and lesser-known spots are just as worthy of a visit.

Best Bet 2026

Chicago was chosen as a Travelzoo Best Bet for 2026. Only ten worldwide destinations were selected for this honor, based on factors like increased interest among Travelzoo members, sustainability considerations or landmark events for the new year. See the full list here.

Best Bet 2026

Best Bet 2025

Best Bet 2026

Lollapalooza | credit: Taylor Regulski

Rose Mary | credit: Matt Haas

Guichard Gallery

In Portage Park, the National Veterans Art Museum’s collection of powerful and moving exhibits offers insight into veterans’ experiences. And in Pilsen, pair an afternoon at the National Museum of Mexican Art with a walking tour to see the neighborhood’s vibrant murals honoring the local community. (Stop by Xurro for a churro and cafe con leche, the perfect afternoon treat during a day of exploring.) The DuSable Black History Museum sits along the edge of Washington Park’s vast green space. The museum was founded nearly 65 years ago and has collected over 15,000 artifacts including paintings, memorabilia and more. Down the road in Hyde Park is the Robie House, a UNESCO World Heritage site designed by legendary architect Frank Lloyd Wright. Tours are available to learn more about this influential Prairie-style home.

As the unofficial culinary capital of the Midwest—and certainly one of the top spots in the country—you’ll want to pack your appetite. From $5 Chicago dogs to Michelin star restaurants, the food scene has something for any taste, budget and style. But it’s not just the options that impress: it’s also the quality. With such a high concentration of great cuisine comes a lot of competition, and you’d be hard pressed to find a dish that doesn’t knock your socks off. Chicago’s reputation attracts a lot of culinary talent, which means exciting new restaurants are always popping up. Dozens of James Beard Awards have been given to the city's restaurants and chefs. Chicago is even the host of the annual award ceremony gala through 2027. In Andersonville, Little Bad Wolf’s diverse menu includes lumpia, bao, tacos and melt-in-your-mouth burgers (worthy contenders to top the list of the city’s best). Head to West Loop, a former industrial area turned trendy restaurant hot spot, to try another competitor for the best burger in the city at Au Cheval. Here you’ll also find the recently opened Adalina Prime steakhouse; and La Scarola, a staple Italian restaurant that’s been around for decades. Bring your group to Demera Restaurant in Uptown for an evening of Ethiopian cuisine, where the exciting flavors and soft injera are best shared with family and friends.

In Bucktown, the French bistro Le Bouchon may leave you second guessing if you actually booked a flight to Paris. Try the classic French dish steak frites “Manion style.” Named after how Chicago chef John Manion ordered this dish, the style includes sliced steak set over the fries with au poivre sauce on top. For brunch, you can’t go wrong with the locally beloved Lula Cafe in Logan Square. Indulge in one of their unique signature dishes, Pasta ‘YiaYia’—made up of bucatini and feta with garlic, brown butter and cinnamon. And for a truly elevated experience, Alinea in Lincoln Park will keep you on your toes during every course.

Chicago has many food staples—more than just the typical deep dish pizza, Chicago style hot dog and Italian beef sandwich (though all are required eating). The jibarito is a Puerto Rican-inspired sandwich created locally, made on plantains instead of bread. Find them at Puerto Rican restaurants around the city, like Marina’s Bistro and Rum Bar in Uptown. Ricobene’s on the South Side is a local institution famed for its hefty, breaded steak sandwich with red gravy. One bite in and you’ll be thinking to yourself “where has this been all my life” (and also, “I should have grabbed more napkins”). The Original Rainbow Cone is a dream dessert for any sweet tooth: sliced layers of chocolate, strawberry, Palmer House, pistachio and orange sherbert ice cream stacked high into a cone or a cup. In 2026, the company will be celebrating a century since the first location opened in Chicago.

It’s never a bad time to visit, because there’s simply always something happening. Chicago is home to nine major league sports teams: men’s and women’s basketball and soccer, football, hockey, rugby and two baseball teams. New in 2026, the Chicago Stars of the National Women’s Soccer League will be moving closer to the city, calling Evanston's Northwestern Medicine Field at Martin Stadium home. Year-round professional sports means home games are never more than a few days away. Whether or not you root for (or actively against) the hometown teams like the Chicago Cubs, catching a game in the “Friendly Confines” is undeniably cool. Opened in 1914, Wrigley Field is the second-oldest MLB ballpark. It has retained much of its tenured charm, with ivy-covered outfield walls and a scoreboard that’s still operated by hand.

There are over 250 theaters in Chicago, from the glitzy and ornate throughout Chicago’s Theater District to the intimate and unsuspecting scattered amid the city. Look to Broadway in Chicago for the big-name productions coming to town, like “Hamilton” at the CIBC Theatre next March-April, and “Les Misérables” at the Cadillac Palace Theatre in May. Practice your “yes, and ...” catch an improv show at The Second City. Famed alumni include Jim Belushi, Chris Farley, Tina Fey and Amy Poehler. The Music Box Theatre opened in 1929 on Southport Avenue and offers cinephiles a lineup of cult, classic, foreign and independent films. Its original theater brings you back to another time, with stucco walls, a grandiose red velvet curtain and a night sky of twinkling stars and clouds on the ceiling. You won't believe your eyes when The Hand & The Eye opens in the Gold Coast neighborhood's McCormick Mansion next year, said to become the world's largest magic venue.

Chicago is fortunate to count itself as one of the top must-stop spots on most major musical artists’ tours. But beyond the headline acts, the real magic happens at the historic and unique venues across the city. The Green Mill has live music every night of the week. Situated on Broadway in Uptown, the cocktail lounge is known for being an iconic jazz destination, said to have been frequented by Al Capone. In Lincoln Park, the Kingston Mines blues club has been around since 1968. Formerly a Morton Salt complex, the Salt Shed opened its doors to an indoor and outdoor concert space in 2022. And not to worry, they preserved the iconic Morton Salt sign on the roof (a sight you’re sure to have seen if you’ve ever driven on the Kennedy Expressway). Pair an evening of live music with a stop into one of Chicago’s countless dive bars like L&L Tavern in Lakeview, Old Town Ale House near The Second City and Nisei Lounge in Wrigleyville, just to name a few. They're all delightfully divey, and as good a place as any to try a Chicago Handshake: that is, a can of Old Style beer and a shot of Malört (a liquor unique to Chicago known for its ... acquired taste).

Like we said earlier, it's always a good time to visit Chicago—even in winter. There's something wonderfully romantic about the sun glistening off the frozen river and a soft, quiet snowfall blanketing an otherwise bustling downtown. That said, after the winter season, locals do not take a day above 50 degrees for granted. Chicago has ample outdoor space and has even gotten creative with adding more. The 606 is an elevated park and 2.7-mile trail built on a former industrial rail line. The trail connects four neighborhoods on the city’s west side: Wicker Park, Bucktown, Logan Square and Humboldt Park. Within the city, green spaces like Grant Park, Millennium Park, the aforementioned Jackson Park and Lincoln Park offer a place to stretch your legs beside skyscrapers and brownstones. The latter is home to the Lincoln Park Zoo. Free and open every day of the year, you’ll see a variety of animals from aardvarks to zebras.

The Chicago River is the focal point of the city’s downtown, with towering skyscrapers rising along the banks of the river and dozens of moveable bridges above keeping the city going. Along the water is the Chicago Riverwalk with a variety of cafes and bars where you can sip on a beverage while the boats float on by. To take in the sights from a different point of view, try kayaking the river. Rentals are available from companies like Urban Kayaks. And beloved by locals and visitors alike, an architecture boat tour is the perfect way to enjoy a nice day on the water accompanied by stories of Chicago’s history and renowned skyline. In fact, Chicago was home to one of the first skyscrapers ever. The (since demolished) Home Insurance Building, completed in 1885, was 138 feet high and considered a trailblazer due to its use of cast iron.

If you’ve never visited before, and you’re not familiar with the region, you may look out the plane window while landing and wonder “what ocean is that?” The Great Lakes defy expectations typically placed on lakes, and Chicago gets to call part of Lake Michigan its own. The city has 26 miles of shoreline, and 18 of those miles make up the Lakefront Trail. Lace up your shoes to go walking or running or rent a Divvy Bike (the city’s bike share system) to cruise the paved lanes. Sprinkled along the shoreline are sandy beaches, on par with what you’d find on the east and west coasts, without the salt and sharks. Here you can swim, go kayaking or paddleboarding, or even rent a jet ski. If you’re staying downtown, Oak Street Beach and Ohio Street Beach are your closest options. Venture further north for Montrose Beach, the city’s biggest, which sits next to the Montrose Point Bird Sanctuary, athletic fields and a fenced-in dog beach. No matter how you plan to enjoy the water, consider getting up early one morning to start your day with an epic Lake Michigan sunrise.

It's always a good time to go to Chicago (yes, winter included). With two international airports, you can fly in on one of the hundreds of nonstop flights. Or, road trip along Route 66 and check out the starting point of the iconic highway (celebrating 100 years in 2026). The highly anticipated Obama Presidential Center is set to open next year, plus new entertainment, show lineups and more. Read on to see why Chicago should be on your list for 2026.

Chicago Riverwalk

But you don’t need to necessarily enter museum doors to experience Chicago arts and culture—one of the best ways is to simply take a walk through the neighborhoods. You can find it in the rainbow sidewalks that adorn Northalsted, the Nine Dragon Wall sculpture that welcomes you into Chinatown and the colorful murals lining West Town.

Public art in Pilsen

One thing about Chicagoans is that they know how to celebrate. Early in the year, Chinatown rings in the Lunar New Year with a parade, and the Chicago River is dyed green in celebration of Saint Patrick's Day. Andersonville embraces its Swedish roots with Midsommarfest in June featuring lots of live music, good food, community and flower crowns. The Tacos y Tamales festival in Pilsen deliciously delivers exactly what the name suggests every July, and iconic music festivals like Lollapalooza, Riot Fest and Chicago Blues Festival round out summer. In October, the city cheers on over 50,000 runners at the Bank of America Chicago Marathon. On Halloween, the Haunted Halsted Halloween Parade’s costume competition makes for an impressive spectacle of creativity. In November, the cherished Christkindlmarket Chicago makes its return. The tradition began downtown in 1996, and in recent years has expanded to Wrigleyville and Chicago’s suburbs. Inspired by the traditional German Christmas markets, you can expect rows of stalls selling sparkly ornaments and festive decor; European comfort foods like bratwurst, fresh pretzels and raclette; and Glühwein, a traditionally German hot, spiced wine perfect for warming up on a chilly winter night.

Lollapalooza | credit: Taylor Regulski

Demera Restaurant

Maggie Daley Park

Jackson Park

Lincoln Park

Bank of America Chicago Marathon

arts & culture | a culinary capital | festivals & entertainment | great outdoors

Jackson Park, home to the future Obama Presidential Center

Rendering of the Obama Presidential Center