SEE & DO
27. Take a selfie in The Bean. It sounds ridiculous, but it’s a funny photo op that literally every other tourist will be doing. It’s a fun souvenir photo to take from your time in Chicago. (I have three bean selfies myself.) The Bean is in Millennium Park, which is also a great place to explore.
28. Navy Pier is a given. I’m going to say to go for the Ferris wheel. No other place will give you the view that the top of the Ferris wheel gives you for the price. Not to mention it’s incredibly romantic, just don’t rock the car. They also do fireworks every Wednesday and Saturday during the summer that are free to the public, so make sure to stick around and check out the display.
29. Take a dinner cruise on Lake Michigan. Discounts are routinely offered, and it’s a great way to check out the city at night. Odyssey Cruises comes highly recommended, and they offer special cruises under the fireworks and at the full moon.
30. If you want to get a unique and well-informed view of Chicago’s architecture, hop on a tour with the Chicago Architecture Foundation. They offer both water and land tours, so you can choose the kind of tour that fits your needs. They’re all staffed by volunteers that are dedicated to preserving the art and architecture of the city, so you’re guaranteed to get a knowledgeable guide.
31. Check out a musical while you’re here. Next to New York itself, Chicago is a great place to catch a fantastic musical. If you like Broadway In Chicago on Facebook, you can check their page on the 25th of every month for $25.00 tickets to certain shows. See something on a Broadway tour (Les Miserables was playing when I went last) or pop by an off-Broadway show; you’re sure to see something great.
32. The Chicago History Museum throws historically themed bar crawls through the city that you can hop on in advance, just in case you want to learn something while you drink. The next event is on Prohibition Era Chicago, with stops at former speakeasies throughout the city. The themes rotate throughout the year, but the crawl usually goes every month at the minimum.
33. Eataly in Chicago is one part restaurant and one part open-air market. The restaurant features fresh Italian food, and the market sells the components to make said food. It’s filled with cheeses and breads with a variety to rival Italy’s. Check it out every day at 10 a.m.
34. This list wouldn’t be complete without something named after Abraham Lincoln (Illinois loves naming things after him), and Lincoln Park fits the bill nicely. It’s Chicago’s largest park, stretching for several miles along the shores of Lake Michigan. It houses the History Museum, Lincoln Park Conservatory, a lakeside theatre that does free outdoor performances in the summer, and the Lincoln Park Zoo. It’s the second most visited park in the United States.
35. If you’re not afraid of heights, take on the Willis Tower (Sears Tower) Skydeck. Located at the very top of the tower, the clear glass floor gives a view of the sheer drop down into the city. There are also plenty of windows, so you can stand safely back on the carpet if you don’t want to take on the ledge. You can even have your wedding up there.
36. Shedd Aquarium is another given for Chicago visitors. It’s easily the largest and most diverse aquarium in the state, and admission grants you access to some of the world’s coolest fish. Plus you can pet a stingray if you’re brave.
37. If you like architecture, take a walkthrough of the Rookery Building. It’s one of best examples of Frank Lloyd Wright’s architectural design in the city, and it’s absolutely beautiful. If you want to see more of his work, his house is a Metra train ride away in Oak Park.
38. Grant Park houses Millennium Park, The Art Institute of Chicago, and Buckingham Fountain, as well as facilities for outdoor concerts and theatre performances. I’ve talked about Millennium Park and The Art Institute, but Buckingham Fountain deserves a mention as well. It’s one of the largest fountains in the world, and was actually designed in a wedding cake style! April through October light shows run at night from 9 to 10 p.m., and a water show starts up every 20 minutes throughout the day.
39. Chicago Lakefront Trail follows along the lakefront, as the name suggests. It’s a nice quaint trail that’s used for walking, running, and cycling. If you want to take a break from the action to just walk around, or if you want to log some cardio on your honeymoon, this is the place to go.
40. If you’re a classical music enthusiast like myself, you have to see a performance by the Chicago Symphony Orchestra while you’re in the city. They perform a variety of music in the historic Symphony Center, and there isn’t a bad seat in the house.
41. Just walk by the Chicago Tribune Tower on Michigan Avenue. It’s the home of the Chicago Tribune (obviously), but the exterior has pieces of buildings from all over the world, including the pyramids!
42. For the best art experience in the city, hit up The Art Institute of Chicago. They feature exhibits from around the world, as well as a “Chicagoisms” exhibit that keeps things close to home. Go to get a broad taste of what the Chicago art scene has to offer.
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