The United States is home to dozens of “bucket list” cities—places you simply have to see when you have the chance. While people often prioritize New York, Los Angeles, and Miami, don’t leave out Chicago! This midwestern gem is more than just a concrete jungle. If you consider yourself well-traveled, it’s likely you’ve already been here, and you know Chicago is an excellent place for people of all ages, especially over-60 travelers. Having been born and raised just 80 miles northwest of the city, I’ve been to the Windy City countless times over the years and continue to be excited to visit time and again. Make it a point to get to wonderful Chicago and try these can’t-miss attractions and activities.
City and Lake Views at Navy Pier
You can’t see Chicago without stopping by the famous Navy Pier. This attraction is over 100 years old and stretches over 3,000 feet into Lake Michigan. Here, you’ll find parks, gardens, boutiques, restaurants, and amusement park rides, all against a backdrop of skyscrapers. Navy Pier is a hot spot for families, but it certainly won’t disappoint a solo traveler! It’s basically a one-stop shop for a great day out, similar to the Mall of America.
Take a Selfie at The Bean
When you’re on a Chicago trip, visiting The Bean is a no-brainer. Officially called Cloud Gate, The Bean is one of the city’s and Midwest’s most famous landmarks. It’s right in the heart of Millennium Park, and whether you’re a local or a tourist, it’s a spot you’ve got to check out! The Bean is known for being a one-of-a-kind photo op, so don’t forget to grab a selfie or ask a kind stranger to snap a pic.
Stroll Chicago’s Iconic Magnificent Mile
Chicago’s Magnificent Mile is a must-see for anyone visiting the city. This stretch of Michigan Avenue runs from the Chicago River to Oak Street and is packed with everything you need for a great day out. The Magnificent Mile has you covered if you’re in the mood for any of the following:
- High-End Shopping—Do you have a taste for luxury? You’ll find a mix of high-end stores like Gucci and Louis Vuitton, as well as popular brands like Nike and Apple, along the Magnificent Mile. You might also stop at a classic department store, such as Nordstrom or Bloomingdale’s while you’re in the neighborhood.
- Delicious Eats—When you’re ready to refuel, there are tons of dining options. Grab a deep-dish pizza at Giordano’s, reserve a seat at a luxe steakhouse, or indulge in a sweet treat from Ghirardelli. And jump in line for legendary Garrett’s Popcorn.
- Sightseeing Spots—The Magnificent Mile is just a stone’s throw away from some Chicago landmarks. Don’t miss the historic Water Tower, one of the few buildings that survived the Great Chicago Fire, and make a stop at the 360 CHICAGO Observation Deck. The Tribune Tower and Wrigley Building are also iconic tourist destinations.
Get a Bird’s-Eye View from The Willis Tower
Are you scared of heights? Even if so, I promise you won’t want to miss the view from the Willis Tower—locals still refer to it by its original name, Sears Tower. You’ll see Chicago like never before. On a clear day you’re likely to even see a few other states in the distance.
I’m definitely glad I had my photo taken overlooking the ledge. I highly recommend paying a little extra for the expedited ticket, too. This allows you to zip all the way to the top without waiting in humongous lines—perfect for over-60 folks who don’t want to deal with the hassle!
See a Show at the Chicago Theatre
The Chicago Theatre should definitely be on your itinerary! Opened in 1921, it’s famous for its stunning architecture and the iconic marquee that lights up State Street. This historic venue hosts a variety of shows, from concerts and comedy acts to Broadway productions and special events. When you step inside, you’ll be wowed by the grand lobby, intricate details, and the huge auditorium that seats over 3,500 people. It’s like stepping back in time, but with modern performances that keep things fresh and exciting. The architecture is just as stunning as you’d expect of opulent European countries like Switzerland!
Even if you’re not catching a show, the theater offers tours where you can learn about its rich history and get a behind-the-scenes look at this architectural gem. Plus, it’s located in the heart of downtown, so it’s easy to fit into your sightseeing schedule. If you’re interested in delving deeper into Chicago’s arts and culture scene, try these locales:
- The Steppenwolf Theatre—Known for groundbreaking productions and famous alumni like Gary Sinise and John Malkovich.
- Broadway in Chicago—Brings hit Broadway shows to the city, with venues like the Cadillac Palace Theatre and the CIBC Theatre.
- Chicago Symphony Orchestra—One of the top orchestras in the world, music lovers will love the chance to hear it in person.
- The Joffrey Ballet—A premier dance company in the Midwest, the Joffrey Ballet is known for some of the world’s greatest performers.
- Lyric Opera of Chicago—Hosts grand operatic performances in the stunning Civic Opera House.
- Chicago Cultural Center—Offers free art exhibits, performances, and cultural events, all in a beautiful historic building.
Learn Something New at a Downtown Museum
Chicago’s downtown is packed with must-see museums. The Art Institute of Chicago, with its amazing collection of classics and modern pieces and those iconic lions at the entrance, is a top pick. The Field Museum lets you explore natural history with immersive exhibits about dinosaurs, fossils, and geology. Other favorites include:
- Shedd Aquarium—Here, you’ll see everything from sharks and stingrays to vibrant coral reefs. Don’t miss the live aquatic shows and the cute penguins. It’s a fun and educational spot for all ages!
- Adler Planetarium—Head to the Adler Planetarium to explore the stars and beyond. Check out immersive exhibits on space exploration, and catch a show in the dome theater. It’s the perfect place for anyone curious about the cosmos.
- DuSable Black History Museum and Education Center—Located in Washington Park, this museum is packed with exhibits celebrating African American culture and history. You’ll find everything from powerful art pieces to historic artifacts and interactive displays. The museum is named after Jean Baptiste Point du Sable, a Black fur trader and Chicago’s first non-Indigenous settler.
- The American Writers Museum—The American Writers Museum is a must-visit for book lovers. Discover exhibits on famous American authors, interactive displays, and fun writing activities. It’s a fantastic way to dive into classic literature.
- Chicago Architecture Center—Get to know Chicago’s famous skyline at the Chicago Architecture Center! You’ll learn so much about the city’s iconic buildings, take a guided tour, and check out detailed models.
- The Money Museum—Do people still collect coins? If you’re interested in rare coins and bills, the Money Museum can’t be missed. You’ll learn about how money is made and even hold a bar of gold!
- Museum of Contemporary Art—Located near the Magnificent Mile, the MCA features remarkable works from both local and international artists. The exhibits change frequently, so there’s always something new to see.
Many of these museums are close to one another, so solo travelers can easily hop from one to the next. However, make sure you check admissions requirements, as some ask you to have a timed reservation.
Relax on the Water
Check out Chicago’s dazzling skyline from a nautical perspective! The city offers plenty of opportunities for fun on the water, whether it’s having a beach day with breathtaking skyline views from downtown’s Oak Street Beach or checking out the river when it’s dyed green for St. Patrick’s Day. Choose from charter boats, dinner cruises, or, my favorite, the Sunset Architecture cruise along the Chicago River. It will not disappoint! By the way, Chicago’s celebration of St. Patrick’s Day is an event unparalleled in the U.S.
Get Wild at the Lincoln Park Zoo
You might not be able to go on a full-on African safari in the Midwest, but you can catch a glimpse of some of the world’s most majestic animals. Chicago’s Lincoln Park Zoo is one of the oldest zoos in the country and is home to animals of all kinds. The best part? Admission is always free! Over-60 visitors will enjoy the zoo even without kids, walking the beautiful garden paths and enjoying what the earth has to offer.
Feel Wanderlust in Chicago
Chicago may not be the far-off, tropical destination we think of when we picture ourselves on vacation, but that doesn’t mean the city isn’t worth visiting! I’ve loved every one of my stays in Chicago, and I love encouraging fellow travelers to schedule trips to U.S. destinations in addition to international ones. Even if you’re traveling without a passport, you can still feel that giddy feeling of wanderlust! Catch more of my travel recommendations on Instagram.