Chicago

10+ Things to Do in Chicago for Solo Travelers

By Nicole Muto

Chicago is one of the great American cities, filled to the brim with history, rich culture, unique art, and attractions. It's the perfect place to visit on a solo trip, especially as it's a walkable city with great public transportation options. 

Sometimes traveling alone can feel overwhelming, but not to worry, we've put together the perfect list of things to do and see on your solo trip to the Windy City. Make the best of your trip by visiting some of the best attractions in Chicago, like... 

  • Skydeck Chicago 
  • Shoreline Architecture River Cruise 
  • Millennium Park 
  • Magnificent Mile 
  • Museum Campus 
  • Art Institute of Chicago 
  • Bike and Roll Chicago Bike Rentals 
  • Chicago Theatre Tour 

All of these attractions and sights are perfect for solo travelers. You'll be able to explore the history and culture of the city on your own schedule and really decide what you want to do. 

Chicago

Getting around Chicago

Chicago is super easy to navigate. Neighborhoods are easily explored on foot (though can be far apart), there are tons of taxis and shared-ride services available. The public transportation system, known as the L, is very reliable and can get you just about anywhere. 

Hop-on, hop-off tours: A Hop On Hop Off Big Bus sightseeing tour is a great way to get acquainted with the city and visit popular attractions. Tours follow a specific route and schedule, so plan accordingly if you have timed tickets or reservations. 

Chicago Transit Authority (CTA) sells visitor passes, available in 1, 3, and 7-day increments that offer unlimited rides on all CTA trains and buses. Check the CTA website for fare info, travel alerts, and trip planners. Most popular attractions are more accessible by bus than the L. 

The L train, Chicago

SkyDeck Chicago

The perfect way to see the entire city is from the top. Journey up to the 103rd floor of Willis Tour for unmatched views of the Windy City from the fabulous Skydeck Chicago. You'll be able to explore the interactive exhibits that provide a history of the building and the city. Then you can step out onto The Ledge, an external, all-glass balcony. 

SkyDeck Chicago offers some of the best 360-degree views of the skyscraper-filled metropolis. Make sure to snap a few selfies while you're there! 

Skydeck Chicago

Shoreline Architecture River Cruise

History buffs and art lovers alike will enjoy this informational Shoreline Architecture River Cruise down the Chicago River. Chicago is well-known for its unique architectural styles and many famous architects have flourished in the Windy City.

As you sail down the river surrounded by stunning buildings, your guide will provide a history of the most famous landmarks in the skyline. It's the perfect way to spend a sunny day and learn more about the city.

Chicago river cruise

Chicago Museum Campus

Taking up a cultural quarter of Grant Park, Chicago's Museum Campus is a 57-acre stretch along the Michigan Lake waterfront that is home to some of the city's best cultural institutions. Want to learn more about our history as human beings? Try The Field Museum. With hundreds of interactive exhibits, you'll journey from the first documentation of humankind to the future of our species. 

For animal lovers, the Shedd Aquarium is a can't-miss. It's one of the most diverse aquariums in the country with 32,000 inhabitants from all over the world. Make friends with aquatic animals, see colorful fish from the Caribbean, and meet dolphins and beluga whales.

And of course, for those intrigued by the galaxy and our planet, visit the Adler Planetarium. With endless planetarium shows, interactive exhibits, and educational talks, there's plenty to learn when the Universe is at least 91 billion years across. 

The Field Museum

Art Institute of Chicago

Consistently voted one of the top-rated museums in the country by TripAdvisor, the Art Institute of Chicago is a must-see for any visitors to the Windy City. Peruse modern art, contemporary styles, architectural marvels, design and photography pieces, and much more. Some of the most famous pieces at the Institute include the Chagall America Windows stained glass windows, Matisse's Bathers by the River, and Georgia O'Keeffe's Black Cross, New Mexico.

Art institute of Chicago

Get around on two wheels

If you want to make the most of your time in Chicago and get around to as many landmarks as possible, rent a bike! Set out on a self-guided bike tour around the city with Bike and Roll Chicago. Bike along the Chicago River, head over to Grant Park, or cruise through the different sculptures and art installations at Millenium Park.

Renting a bike will provide an easy and fun way to get around the city, and with your 4-hour pass to use the bike, you'll no doubt see everything on your bucket list.

Bike ride Chicago

Chicago Theatre

If you're a fan of the arts, theater, history, or all three, then you have to take a tour of the world-famous Chicago Theatre.

The Chicago Theatre is known for hosting a spectacular lineup of stars like Dolly Parton, Dean Martin, and Frank Sinatra. From concerts to Emmy-winning theater productions, this magnificent theater is a huge part of Chicago's history.

Chicago Theatre

Millennium Park

This spot is the green heart of urban Chicago. From vast open spaces for walking, relaxing, and playing to an eclectic variety of ever-changing special events, festivals, and performances, there's something for everyone at this iconic park. 

The park is most famously known as the home of the Cloud Gate Sculpture - aka The Bean. You can't visit Chicago without stepping in front of the gigantic art installation and snapping a selfie. Grab lunch to go and head over to the park for an impromptu picnic full of people-watching and relaxation. 

Cloud Gate The Bean

Chicago River Walk

Another relaxing way to spend some time in Chicago is to walk the picturesque strip that lines the river. Enjoy a stroll down the south bank of the Chicago River and stop in at one of the many restaurants and shops lining the River Walk, or simply enjoy the stunning architecture. This is the home of the skyscraper, after all. 

Chicago river walk

Magnificent Mile

The Magnificent Mile district is the area immediately surrounding North Michigan Avenue and a popular destination for visitors with many of the city’s hotels, shops, restaurants, bars, attractions, and more. 

There are more than 50 landmark structures you can find on this strip - from the 360 CHICAGO observation deck to Navy Pier and its Centennial Wheel. Enjoy iconic spots and try some of the top-rated restaurants and rooftop bars here. 
 

Magnificent Mile

Have a wonderful solo trip to Chicago!

There you have it. Our list of some of the best things to see and do on a solo trip to Chicago. We hope you consider adding some of these fantastic spots to your Chicago bucket list. While traveling alone may seem scary at first, you may find it to be one of your favorite experiences. 

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A visitor takes in the Chicago skyline
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What to do in Chicago in October

Regularly marked out as one of the best times to visit, Chicago in October boasts a packed diary of events without the massed ranks of summer leaving you feeling lost in the crowd. Temperatures start to drop, but the sun still has enough warmth in its rays to allow you to explore the epic fall foliage or delight in the multitude of Halloween-inspired activities that take place towards the end of the month. Need some inspiration for what to do in Chicago in October? We’ve got it in bucketloads!   Save in Chicago in October October is a great time to visit Chicago. The heat of summer may be gone for the year, but so are the biggest crowds, leaving the city feeling much more breathable for anyone looking to take advantage of the huge array of events that take place. But don’t forget about Chicago’s year-round attractions, because by traveling with Go City you’ll make massive savings on admission costs to many of them! So grab a Chicago attraction pass and save while you see the city!
Ian Packham
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Romantic Things to Do in Chicago - Valentine's Day & More

Looking to plan a romantic getaway with your sweetheart? There are so many wonderfully romantic things to do in Chicago that it’s hard to choose our favorites. If you’re looking for romantic things to do in Chicago, either for Valentine's Day or for a romantic trip any time of year, check out a few of our top suggestions. The Signature Lounge at Hancock Center Located atop the well-known John Hancock Center you'll find the romantic cocktail bar known as The Signature Lounge. The view from the 96th floor is phenomenal (to say the least), and the food and drink are equally exquisite. This is the perfect spot to wind down after a busy day or get geared up for a romantic evening out. Keep in mind that this venue is in high demand, and will both fill up quickly and come at a high price per drink. (I, for one, tend to limit myself to sipping a single drink slowly to enjoy the view.) If you'd like the take this evening to the next level -- literally -- a visit to 360 CHICAGO (just a bit lower on the tower) is a delightful addition to a romantic drink or two. You'll get to see the city skyline from above, including the shoreline of Lake Michigan and the easily identifiable Navy Pier Centennial wheel. Skydeck Chicago (top of Willis Tower) Looking out from the Skydeck Chicago observation deck at the top of the Willis Tower (formerly Sears Tower) is one of the most romantic things to do in Chicago. You'll enjoy 360-degree views from the second tallest tower in the western hemisphere, taking your love to new heights in a serious way. For the most romantic view, head to the Skydeck at sunset or after dark when the city lights are glowing. Explore the Art Institute of Chicago If you’re a fan of art, then there are few places as romantic, in Chicago, as the #1 rated museum in the country, the Art Institute of Chicago. They’ve got some of the best collections of Impressionist Art, some gorgeous Chagall stained glass windows, plus an impressive array of sculpture, textiles, antiquities and more. Check out their seasonal special exhibits for details on new and exciting things on display right now, or hit up their permanent collections for a few love-themed pieces like their collection of 19th century Valentines and sexy photographs. Centennial Wheel at Navy Pier This 15-story Centennial Wheel is located at one of the most visited attractions in Chicago, at the exciting Navy Pier. Recently redesigned as part of their centennial project, the Centennial Wheel offers beautiful sights at thrilling heights. You can even enjoy free days once per month! From the top of the famous Centennial wheel, you and your partner will escape the crowd for a few minutes for some alone time with the scenic skyline and Lake Michigan views. After you disembark from the Centennial Wheel, Navy Pier is a lakeside wonderland to explore. You'll find romantic restaurants, shops, and other top-class attractions as you stroll along with your loved one. If you plan it right, you can even pick up tickets to a show at the well-regarded Shakespeare Theater, also located on the Pier. Attend a Show Chicago’s theater scene is pretty unbeatable when it comes to variety and quality of performances. From the traditional (like you’d find at the Shakespeare Theater on Navy Pier) to the avant-garde, there’s something for all tastes. Because a theatrical performance is a pretty hot idea for Valentine’s Day, be sure to secure tickets in advance! You may be able to find discounted tickets by signing up for theater-specific mailing lists and websites like Goldstar. Stroll the Beautiful Parks While Millennium Park is often the favorite for cultural activities and current events, Grant Park has just as much in the way of sightseeing and beautiful scenery. Or, check out the Lurie Garden to find the hidden beauty of wintertime plants. Whichever venue you choose, the real treasure is in the journey. If you’re planning a date in the warmer months, be sure to check out Buckingham Fountain, a truly impressive array of water jets set against the impressive Chicago skyline. Of course, if you're visiting during the winter months around Valentine's Day and can't bear the Chicago winter cold, then a visit to the Chicago Botanic Garden is another nice option. Stick with their indoor exhibits to see some lovely tropical plants and flowers. Enjoy a Romantic Meal A romantic dinner is a classic for a reason. It’s hard to go wrong with a well-researched dinner venue this time of year, especially if they’re offering special Valentine’s Day meals or menus. It’s a great break from your own cooking and a good way to pry yourself away from Netflix. Downtown Chicago has tons of great restaurant options, many of which are in easy distance of several other great attractions to help you plan a larger itinerary. Remember to book your table early on a site like OpenTable to avoid last-minute panic! Remember to Save on Attraction Admission So there you have it. Our list of some romantic things to do in Chicago, just in time for Valentine's Day. Remember, some of these great options are included on the All-Inclusive Pass and the Explorer Pass from Go City, where you can save up to 55% on combined admission vs paying at the gate.
Katie Sagal
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Fun Facts About Chicago: Your Essential Trivia

How much do you know about Chicago? Test your knowledge of the Windy City with our trivia below. These fun facts are sure to come in handy on your Chicago vacation! Top Chicago facts 1-10 The world’s very first skyscraper was erected in the city in 1885. Skydeck Chicago is a film star! Catch a glimpse of the experience in Ferris Bueller’s Day Off. The Willis Tower is the eighth tallest building in the world, coming in at 1,450 feet and 110 stories tall. Chicago invented deep-dish pizza. The Navy Pier Centennial Wheel was preceded by an iconic Ferris wheel, which welcomed over 17 million riders in its ten-year life span. Historic Route 66 begins in Chicago (and terminates in Santa Monica, CA). The Field Museum’s newest addition is Máximo the Titanosaur: the largest dinosaur ever discovered, weighing 70 tons. Chicago is known as “The Windy City” for the bombast of its politicians—not for its weather. Chicago is home to an impressive 56 museums, including the famous Art Institute of Chicago. The Taste of Chicago — a summer legend in Chicago — is the world’s largest free outdoor food festival. Top Chicago facts 11-20 The Museum of Contemporary Art is the only museum in the city to feature dozens of works with the title, “Untitled.” Batman’s iconic Gotham City was based on Chicago; not, as many people assume, NYC. The Lincoln Park Zoo is one of the world’s rare free zoos. Malört, one of the most distinctive liquors in the world (and some say the most unpalatable), was created in Chicago. Today, more than 90% of the national consumption of Malört is still confined to the greater Chicago area. The Adler Planetarium was America’s first planetarium. The Adler Planetarium is also one of the best places to get a great view of the skyline. The Museum of Science and Industry is one of the largest science museums in the world, with more than 400,000 square feet of exhibit space. The renowned Pablo Picasso sculpture, created specifically for the city and located in Richard J. Daley Plaza, weighs an intimidating 162 tons. It is also called 'Untitled'. Chicago's Brookfield Zoo was the first such institution in the world to successfully perform brain surgery on a gorilla. The Brookfield Zoo is also known for its majestic fountain, named for Theodore Roosevelt, the 26th President of the United States who is remembered for expanding protections on wildlife. Top Chicago facts 21-25 The Chicago Theater's grand lobby is inspired by the Royal Chapel at Versailles. The Chicago Theater also boasts one of the oldest Wurlitzer pipe organs remaining in existence. The Ernest Hemingway Home was the first house to have electricity in Oak Park. The American Writer’s Museum is the only museum in the world devoted exclusively to American writers and their works. The Shedd Aquarium has more than 32,000 animal inhabitants. Save on attractions Admission to many popular Chicago attractions is included with a pass for Chicago with Go City®. You could make big savings vs paying at the gate. Share your trip with us Follow us on Facebook and Instagram, and share your adventure with us. Tag us at @GoCity and use #GoCityPass on your travel photos to keep us up to date with your vacation!
Katie Sagal

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