Chicago is one of this country’s most important and beautiful cities. Not quite as noisy as New York and not quite as glamorous as Los Angeles, Chicago is a unique city all on its own, with plenty of Midwestern hospitality to go around. Once home to legendary mobsters, Chicago today is better known for its incredible culinary scene, historic museums, and abundant recreational opportunities. Discover the highlights in our guide to things to do in Chicago on an extended stay.
There’s more to Chicago than deep dish pizza and hot dogs
Although Chicago isn’t as glitzy as L.A., you might have a hard time believing that when you visit BLVD in Chicago’s West Loop neighborhood. This eye-pleasing two-story restaurant and lounge boasts an old 1950’s-era Hollywood vibe, complete with an opulent atmosphere, shimmering chandeliers, circular seating, and a decadent menu, within which caviar, seafood towers, thick steaks, and other temptations await.
817 W Lake St.
Chicago might not be the first city to come to mind when you talk about vegetarian fare, but Clever Rabbit’s culinary masterpieces can awaken the mind of even the most steadfast Bears fan. Located in trendy Wicker Park, Clever Rabbit is a veggie-centric restaurant where dishes made from locally sourced ingredients accompany inventive cocktails, a stellar wine list, and a set of vinyl records that reigns supreme.
2015 W. Division
Chicago is home to America’s very first Nutella Café, which quickly became one of the hottest places to eat in the Windy City. But don’t let the name fool you; this café offers much more than Nutella sandwiches. The menu consists of a wide range of sweet and savory items, such as a bacon and cheese strata, artisanal paninis, croissant pancakes, seasonal salads, and even gelato.
189 N Michigan Ave.
Elske is the very first restaurant from David and Anna Posey, both protégés of chef Paul Kahan, and it has Chicagoans going wild. The restaurant serves a variety of different American and Danish dishes determined by the seasonal availability of ingredients, as well as a la carte and tasting menus. Located in the West Loop, Elske features a Danish design, a lovely outdoor fireplace, and an ethereal atmosphere.
1350 W Randolph St.
Split Rail is located in West Town, and it is the brainchild and first restaurant of former Ada Street chef, Zoe Schor. True to Chicago’s nature, this restaurant serves up classic American comfort foods with a creative twist. The fanciful menu features favorites like loaded baked potato gnocchi, a duck in three acts, dry aged prime tomahawk chop, and fajitas reimagined.
2500 W Chicago Ave.
Shopping, museums, comedy, Ferris wheels, and so much more!
Chicago has long enjoyed a partnership with the U.S. Navy as the city is a common place for graduates from the nearby Great Lakes Naval Training Station to spend their time off. And while the Navy Pier isn’t exactly associated with the military anymore, it has since been converted into a one-of-a-kind entertainment center. The Navy Pier is home to a brand-new Centennial Ferris Wheel that lifts riders nearly 200 feet in the air, an IMAX Theatre, the Chicago Shakespeare Theater, and a large selection of stores and restaurants, making it an all-in-one solution for spending a great day off in Chicago.
600 E. Grand Ave.
The Chicago Theatre
Few theaters in the country are as immediately identifiable as The Chicago Theatre. After all, the huge block letters spelling out C-H-I-C-A-G-O on the iconic marquee are hard to miss. Once called “the wonder theatre of the world” when it first opened back in 1921, the Chicago Theatre remains one of the most illustrious theatres in the world. And the show goes on despite its age, with the venue hosting all manner of musical and comedy acts, and arts performances throughout the year. Marquee Tours are also available if you just want to learn more about this legendary Chicago institution.
175 N. State St.
Chicago’s Second City comedy troupe has produced some of the biggest names in the comedy world, including John Belushi, John Candy, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey, and many, many others. Not only does this talented improv company produce hilariously funny sketches, but at the end of every show, the cast members also take ideas from the audience, turning them into one-of-a-kind improv scenes on the spot.
1616 N Wells St.
Art Institute of Chicago
The Art Institute of Chicago is home to one of the finest and most diverse collections of art in the country. The contemporary section alone features masterful works from such esteemed artists as Picasso, Pollack, Dali, Warhol, and Matisse. Meanwhile, the museum’s huge impressionist collection features the largest collection of Monet paintings in the world – and that’s just the tip of the iceberg. AIC also features a significant amount of Asian, American, Native American, African, European, and Byzantine-era works of art in its overall collection. One visit will show you why this museum was chosen as the #1 Museum in the World by TripAdvisor.
111 S Michigan Ave.
John Hancock Observation Deck
The John Hancock Building is one of Chicago’s most iconic structures. And, nothing is quite like the building’s observation deck, which on a clear day can allow you to see up to 80 miles away. This building is the third largest in the city, but thanks to its history, it is the one everyone wants to visit. Believe it or not, it takes just 40 seconds for the building’s elevator to take you from the ground level to the observation deck, which sits 1,000 feet above the street.
875 N Michigan Ave.
Beaches, golfing, and parks – you’ll find more than enough to fulfill your recreational needs
Located in Chicago’s Uptown neighborhood in Lincoln Park, you’ll find Montrose Beach. From sunbathing to swimming to volleyball and a variety of other watersports, Montrose Beach has an abundance of recreational activities to enjoy. At the southern edge of the beach, there is a natural area where migratory birds visit during the fall and spring seasons. There’s also a special dune area that’s designed as a rare “panne” habitat — a flat, wet, and open sandy area for protecting birds and endangered plant species.
4400 N Lake Shore Dr.
Chicago Lakefront Trail
The Chicago Lakefront Trail has 18.5 miles of trails ideal for walking, biking, rollerblading, or jogging. With the Chicago skyline on one side and Lake Michigan on the other, it’s also one of the city’s most scenic spots. Making it even better is the fact that during your excursion on the trail, you’ll pass by several other Chicago landmarks, including Soldier Field, the Navy Pier, Buckingham Fountain, the Lincoln Park Zoo, and the Adler Planetarium.
W. Ardmore Ave. and N. Sheridan Rd. to E. 71st St. and S. South Shore Dr./US 41 at South Shore Cultural Center.
Eugene Field Park
Eugene Field Park sits on more than 12-acres, where it consists of tennis courts, a spray pool, and an outdoor basketball court, just to name a few of its recreational amenities. The park is also home to the Laura Wiley Theater, and a 45-foot by 10-foot exterior clay and ceramic tile mosaic art installation created by 15 local teens.
5100 N. Ridgeway Ave.
With its snowy and windy winter weather, you wouldn’t think that Chicago had a strong golf presence, but this city is home to a number of must-play courses. With three nines, a gorgeous nature preserve-like property, and excellent playing conditions, Cantigny Golf in Wheaton is one of the best the Chicago metro area has to offer. The Glen Club in Glenview is another top-rated course, and no wonder, it was designed by none other than Tom Fazio. This course is especially known for its rolling fairways, drastic elevation changes, and lakes and streams. It’s also home to a massive 48,000 sq. ft. clubhouse, the best one of its kind in the metro area.
Extended Stays in Chicago
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