After visiting Chicago for a long weekend, it comes at no surprise that the Windy City has been dubbed Conde Nast Traveler’s #1 big city in America. Exploding with impressive architecture, art of all kinds, brilliant chefs, and thoughtfully-designed outdoor spaces, this city has something to offer every visitor.
There’s no way you can do it all but to get a little taste of the city, here’s a list of things you can’t miss if you’re visiting Chicago for the first time.
Art Institute of Chicago
Book your entire afternoon for a visit to the Art Institute of Chicago. It is HUGE and there is so many interesting paintings and sculptures to see. A few personal favorites were the contemporary art wing and the Thorne miniature rooms. If you’re an Illinois resident, Tuesdays are free admission!
Millennium Park
Home to the famous Chicago Bean (Cloud Gate), Millennium Park is a public park that spans 25 acres and is filled with flowers, sculptures, and architecture. It’s a fun place to walk around, relax, or have the kids run free or play on the playground.
During the holidays, the city’s official Christmas tree is lit up here at the intersection of Michigan Ave and Washington St, so be sure to check that out if you’re visiting November to early January!
Wendella Architectural River Cruise
The best $40 you will spend your whole trip. This river cruise tour guides give you the full history of Chicago, point out and provide interesting facts about all the amazing architecural buildings on the riverfront, and so much more. No explanation can do this tour justice.
Pro tip: Arrive early especially if going with a large group to ensure you’ll secure seats on the top of the boat. 30-45 minutes early is recommended! Also be sure to arrive at the appropriate dock corresponding to your ticket confirmation as there are several docks and lines, all within walking distance.
Lou Malnati’s Deep Dish Pizza
Founded by the son of Rudy Malnati, who was instrumental in developing the recipe for Chicago-style pizza, this local chain has become one of the Chicago area’s best-known deep dish pizza. When in Chicago, gotta try that deep dish!
Pro tip: They do not accept reservations but you can go in-person to put your name on the list for a specific time to come back and dine in. 10/10 would recommend doing this so you can get the full experience! We checking in around 3 PM and were able to secure a “reservation” at 7 PM.
Explore the Food Scene
While the deep dish pizza in Chicago is a must, there are so many other amazing restaurants and brilliant chefs in the Windy City. A few places I would recommend putting in a reservation for well ahead of time (2-3 weeks minimum) would be:
- London House Rooftop
- Cindy’s Rooftop
- Cira Chicago (pictured above)
- Portofino’s (on Clark)
- Beatnik on the River
- Roka Akor
Navy Pier
At 3,300 feet long, Navy Pier is known as “Chicago’s lakefront treasure.” There is no admission to enter the pier but there are plenty of things to keep the entire family entertained including restaurants, park rides (carousel, ferris wheel, swings, etc.), breweries and more.
During Halloween they light the pier with jack-o-lanterns, in the summer they offer free fireworks shows, and at Christmastime they feature a light garden of large-scale sculptures, an ice rink, and a holiday beer garden. So be sure to check out their website for seasonal events going on during your time of visit.
The Magnificent Mile
The Magnificent Mile is Chicago’s main commercial district that is home to upscale shops, fashion outlets, and cool rooftop hotels. If you’re a shopper, this is basically your paradise as the Magnificent Mile boasts more than 450 retailers. Even as a window shopper you’ll be happy just seeing the architecture of the surrounding buildings including the historic Chicago Water Tower, the neo-Gothic Tribune Tower, and more.
Chicago Riverwalk (or run)
Take a stroll or a jog on the Chicago Riverwalk, a multi-use public space home to many exercisers of all kinds.
If you have any other Chicago must-dos or recommendations, leave them in the comments below or shoot me a message on Instagram @wanderlustletsgo.
