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12 Best Attractions in Chicago | Landmarks to See

12 Best Attractions in Chicago | Landmarks to See

Are you traveling to Chicago as a couple or as a family with kids? If yes, the city is a great option for tourists in both cases. Here are some of the best attractions in Chicago listed for first-time travelers.

Chilly winter, delicious cuisine, stunning architecture, and baseball games are the things you might think of whenever someone mentions Chicago.

However, did you know the 3rd-biggest city in the country has many thrilling activities, both indoor and outdoor, to offer?

river in Chicago with bridges drawn

With amazing landmarks such as Lake Michigan and the Chicago Riverwalk, Chicago is brutally underrated when it comes to adventure-filled vacations.

Whether you’re in love with the greenery and serene waters, or an enthusiast for art and architecture, Chicago can cater to all your adventurous whims. Without further ado, here’s my list of the best attractions in Chicago, to help you plan your next weekend trip.

Best Tours & Activities in Chicago, Illinois

Chicago Segway TourHop on the most innovative tour to hit Chicago in years! Gliding around the Windy City on your very own Segway, you'll see all the famous sights - Buckingham Fountain, Navy Pier, Lake Michigan and more. Be one of the first to take part in this unique, unforgettable experience!
3-Hour Segway Tour of ChicagoGlide around the streets of Chicago on a 3-hour Segway tour. Zip past the cascading fountains of Millenium Park and swoop through Grant Park’s manicured gardens. See Chicago’s towering skyline, the Chicago Lakefront, and much more from your segway.
Chicago River Architecture Cruise: Skip-the-Ticket-OfficeCruise along the Chicago River on a 75-minute tour, and discover hidden architectural gems among the city’s renowned landmarks. Led by a docent providing live narration, the tour passes more than 40 structures, and sails under historic bridges.
Chicago Architecture River CruiseExperience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch of the Chicago River, up the north branch to the East Bank Club, and then south past Willis Tower (Sears Tower) to the old Post Office Building. Take in magnificent city skyline views as you see more than 40 notable buildings, including the John Hancock Center and the Wrigley Building, and learn about their distinctive architecture from your onboard guide, an expert in architecture.
Chicago Walking Tour: Interior Architecture of the Loop and Pedway TourGet an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors of the Marshall Fields Building, Chase Tower, Chicago Cultural Center and more, plus see public art by Chagall and Picasso. Stroll through elegant lobbies, under glittering domes and into the sprawling network of Chicago Pedway tunnels. Your expert guide shares insights about the city’s diverse architectural styles and history, bringing the details of the Windy City into vivid focus.
Loop Interior Architecture Walking: 2-Hour Walking TourStep inside Chicago's magnificent lobbies, corridors, and the underground Pedway System for an in-depth look at the city's architecture and a personal, cultural approach to experiencing downtown. Enjoy at any time of the year!
Chicago: Gangsters and Ghosts 2-Hour Walking TourExploring Chicago from the perspective of ghosts and gangsters. Take a 2-hour history-based guided tour and discover Chicago’s gangsters and ghost stories. See the city’s darker side as you walk through the famous Chicago Loop district.
Chicago City Minibus Tour with Optional Architecture River CruiseDon’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. The small-group atmosphere with maximum of 12 people ensures a more personal experience. The city tour ends at Millennium Park.You also have the option to upgrade to include a 75-minute Architecture Cruise down the Chicago River! This popular open-top boat tour offers the perfect vantage point to admire the city’s renowned buildings.
Chicago Prohibition TourDiscover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the sale of alcohol was banned for more than a decade in the United States, and the subsequent popularity of illicit establishments where liquor, jazz, and mobsters ruled. An air-conditioned coach shuffles you from bar to bar, so feel free to buy a drink or two. This small-group tour, limited to 20 people, ensures a more customized experience with your guide.
Chicago: 75-Minute Architecture Cruise by SpeedboatSee some of the most exceptional skyscrapers and architecture in America on a 75-minute speedboat cruise through Chicago. Cruise Lake Michigan and the Chicago River to get up-close to architectural gems such as Willis Tower and the Lyric Opera.
Go Chicago Card: Save up to 55% on Top AttractionsThe Go Chicago All-Inclusive Card is the best choice for maximum savings and flexibility. Save up to 55% off retail prices on admission to over 25 top attractions and tours including Shedd Aquarium and more.
Chicago: Navy Pier Centennial Wheel Regular & Express TicketSoar to heights of nearly 200 feet over Navy Pier, with unparalleled, 360-degree views of Chicago and Lake Michigan. Choose between pre-purchasing a Regular or a Fastpass Express ticket to experience this iconic part of the Chicago skyline.
Chicago Classic Lake Tour: 40-Minute Sightseeing CruiseSee the sights of Chicago from Lake Michigan on this 40-minute Classic Lake Tour. Admire the stunning views of the Chicago skyline and see many of the city’s iconic landmarks. Learn about Chicago’s history and its architecture during the cruise.
360 Chicago Observation Deck Admission: Skip the Ticket DeskSkip the ticket purchase line to enjoy the best panoramic views of Chicago, 94 stories above the Windy City. Enjoy stunning lake views and close-up vistas of Chicago’s amazing skyscrapers.
Chicago: Hop-on Hop-off Open Top Bus TourThis hop-on hop-off sightseeing tour of Chicago takes you on an extensive route, showcasing the best the city has to offer. The tour travels through Grant Park and Millennium Park, to the city’s top skyscrapers, and to other top attractions.
Skydeck Chicago AdmissionGaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. With mobile tickets, simply scan your phone for direct entry into the SkyDeck
Big Bus Chicago Hop-On Hop-Off TourThe lakeside metropolis of Chicago is famous for its striking skyscrapers, world-class museums and colorful history. Explore the “Windy City” at your own pace, with the choice of a Classic, Premium or Deluxe ticket, all which include a hop-on, hop-off sightseeing bus tour with stops strategically located near the city’s top attractions. Hop on to experience sites like the Adler Planetarium and Navy Pier or hop off along the Magnificent Mile to shop, see the great city at heart-stopping heights from Willis Tower’s Skydeck or visit the Chicago Architecture Center, which is included in the Premium and Deluxe tickets.
Chicago: 90-Minute Mob and Crime Bus TourExperience the darker side of the Windy City on a 90-minute Chicago Crime Tour that introduces you to the history of Chicago’s criminals and gangsters. Escape into the city's underworld while learning about characters like Al Capone and John Dillinger.
Willis Tower Skydeck and The Ledge Experience TicketTreat yourself to an exhilarating view over the whole of Chicago from the top of the Willis Tower. Ride 103 floors to the Skydeck and step out onto The Ledge, a glass-paneled box with vertical views to the ground below.
Chicago Crime and Mob TourSome of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s criminal underworld as you investigate stories about Al Capone, The Untouchables, the Chicago Mob and more. From a luxury coach, see the sites of storied crime scenes including Biograph Theatre, Holy Name Cathedral, and the St Valentine's Day Massacre, one of Chicago's most notorious murders. Snap photos of the historic criminal courthouse, and hop off the coach to walk the path that Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths.

Best Attractions in Chicago for Outdoor Enthusiasts

It’s highly unlikely for a hustling bustling metropolitan city to provide outdoor activity options. But, that’s not the case for Chicago. Check out my list to find out.

  1. Grant Park

I wouldn’t be wrong if I called Grant Park the face of Chicago city. Sitting between the high-end skyline of the metropolitan city and the lakefront, the park is 300 acres of recreational space for outdoor lovers.

Grant Park

What’s more, Grant Park is home to some of the best attractions in Chicago. These include iconic landmarks and monuments such as The Art Institute of Chicago and the Field Museum of Natural History.

Similarly, it has some of the most iconic Chicago attractions for kids, such as the Shedd Aquarium, the Adler Planetarium.

If you want to indulge in all its attractions, you should consider buying a Chicago CityPass to access all Grant Park attractions.

Through their site, you can purchase your tickets beforehand with up to 9 days of validity to tour the park as you like.

Besides that, you can simply enjoy a peaceful outdoor excursion and feast your eyes on the unique greenery and majestic view.

The star of the show is undoubtedly the Clarence Buckingham Memorial Fountain. Here, you can take memorable family photos and enjoy the lakefront view while sipping your favorite beverage.

See Related: Unusual Things to do in Chicago, IL

    2. Lincoln Park

If you’re a US citizen, you’ve probably heard of the Chicago city motto, “urbs in horto,” meaning, “City in a Garden.” Nothing personifies the essence of this phrase better than the exemplary Lincoln Park.

Lincoln Park

While the exuberant nightlife at the heart of Lincoln Park is one of the best attractions in Chicago, it has equally wonderful outdoor architecture.

The immense green park has many walking trails and a tranquil lakefront. This unique combination makes it an ideal place to enjoy outdoor activities, Chicago-style.

For outdoor lovers, a walk through the 1200-acre park while experiencing Victorian architecture and rustic pathways is bound to be an Instagram-worthy excursion.

Furthermore, if you’re looking for Chicago attractions for kids, you can take them to the Chicago Zoo and the Lincoln Park Conservatory to spend a day from your itinerary. All of these attractions are found within the Lincoln Park vicinity.

Similarly, the park is a family-friendly area with wooded areas and trimmed vegetation so that you can enjoy a leisurely day out with your loved ones.

    3. Chicago Lakefront Trail

Of all the outdoor activities Chicago is known for, Lake Michigan is the most celebrated attraction. Chicago’s Lakefront Trail further accentuates the renowned lake.

Chicago Lakefront Trail

The 18-mile trail extends across multiple neighborhoods of the city, making it one of the most scenic routes that cover all of Chicago’s tourist destinations. You can use the trail to run, walk, or bike along the shore of Lake Michigan.

Moreover, you can catch views of the Navy Pier, the Museum District, Grant Park, and the distinct Chicago skyline while walking along the trail.

Similarly, if you buy the Chicago CityPass before venturing across the Lakefront Trail, you can get easy access to any of the tourist spots that appeal to you, and stop to take a look.

However, the trail can get quite crowded if you visit during the afternoon, and it doesn’t have many trees or shades to guard you against the sun. That’s why it’s not the ideal Chicago attraction for kids.

But, if you’re a morning person, this is one of the best attractions in Chicago for you. That’s because the midday sun won’t be out yet, and the trail isn’t too crowded during those hours.

     4. Chicago Botanic Garden

It is easy to get tired of the urban attributes and intimidating skyscrapers in a metropolitan city like Chicago. If you’re facing the same situation, the Chicago Botanic Garden is one of the best attractions in Chicago for nature lovers.

Chicago Botanic Garden

Visiting the Botanic Garden is like taking a breath of fresh air after the hustle of the city. You can simply take a peaceful walk or enjoy a family picnic in the garden while appreciating the natural beauty.

Besides that, if you’re traveling with the little ones, these gardens are the best Chicago attractions for kids. That’s because it is a preserved bird-watching area as well.

They can bring along their binoculars and watch spectacular and unique birds like scarlet tanagers, white-throated sparrows, and yellow warblers.

    5. Chicago Beaches

Beaches are one of the best attractions in Chicago. But, they tend to become quite crowded, making them inconvenient for tourists looking for ideal Chicago attractions for kids.

Chicago Beaches 

But that doesn’t mean you can’t enjoy the beach in Chicago at all. If you’re traveling with family, you can head to the Uptown beaches like Montrose Avenue Beach and North Avenue Beach.

These beaches are more peaceful and secluded as compared to the central city. You can spend your days relaxing on the sand and basking in the sun.

Apart from that, you can indulge in fun outdoor activities like viewing the city skyline and witnessing the enchanting fireworks along the Navy Pier.

Also, you can rent speedboats, jet skis, kayaks, and paddleboards to enjoy thrilling water sports with your kids.

One of the best outdoor activities Chicago offers is the paddleboard yoga class on the beaches. You can stretch out all your stress and worries on the sandy beach and head out on the paddleboard to continue your yoga ritual on the blue waters.

See Related: Do You Need a Car in Chicago?

    6. Millennium Park

Whether you’re a tourist or a local, Millennium Park is one of the best attractions in Chicago for outdoor lovers. While you can have fun enjoying long walks and hikes across the park, it has many other outdoor activities to offer.

Millennium Park

The city holds numerous performances and concerts at the Jay Pritzker Pavilion regularly. You can plan your vacation during the holiday season when the Pavilion has celebrity performances almost every week.

However, with hundreds of performances held throughout the year, you’ll most likely get a chance to join one whenever you plan your visit. Another fun aspect of The Millennium Park is ‘The Bean,’ which makes it one of the salient Chicago attractions for kids.

Officially named ‘Cloud Gate’ by its artist, Sir Anish Kapoor, the monument is a centerpiece of the Plaza at Millennium Park. Since it was unveiled in 2004, “The Bean” has become one of the best attractions in Chicago for tourists and locals alike. Simply said, your Chicago itinerary is incomplete without taking a selfie alongside ‘The Bean.’

Its shiny surface reflects the entire skyline of Chicago effectively. This means you can photograph yourself and your family with the city’s skyline in the backdrop and create memorable photographs for your travel album.

Check out these best Chicago walking tours to see the city on foot.

    7. The Chicago Riverboat Tour

If you love cruising the waters while sipping drinks and enjoying the company of your loved ones, you should consider kayaking across the Chicago River.

Chicago River is a great place

You can hop on the conventional kayak tours for around $20 per person. If you’re traveling in a large group, you can even rent your personal kayak and enjoy a leisurely time together.

First-time visitors can opt for guided tours to discover the historical architecture and quintessential bridges during the river cruise.

Besides that, there are many places across the river where you can rent your kayak. This means you can easily find a spot to rent a kayak close to your lodgings.

See Related: Hidden Gems in Old Town, Chicago

8. Music and Fine Dining at the Jay Pritzker Pavilion

If you’re looking for a romantic night outdoors in Chicago, the Jay Pritzker Pavilion is a must-visit site for you. Located in the vicinity of Millennium Park, the Pavillion hosts free concerts with various genres of music. These include everything from rock to Pacific Afro.

It sports lawn-style seating designed by Frank Gehry. The construction creates an immersive experience for everyone around the stage. You’ll never feel as if you’re too far away from the stage, wherever you’re seated.

Besides that, the Pavilion offers one of the best outdoor dining in Chicago, combined with multiple outdoor movie screening areas. If you want to spend an eventful evening outdoors with your loved one, it has all the best attractions in Chicago for outdoor enthusiasts.

See Related: Best Day Trips from Chicago

    9. The 606 Hiking Trail

For people who like to embrace the outdoors actively, hiking is the go-to adventure sport. But, did you know that you could find a hiking trail in a metropolitan city like Chicago?

The 606 Hiking Trail

The 606 is a unique hiking trail and one of the best outdoor attractions in Chicago. It is an elevated trail that’s built over run-down railway tracks.

The trail takes you through all the historical heritage of Chicago, along with its pleasant neighborhoods and peaceful gardens. You can use the paved trail to walk, run, or bike across the city.

The 606 begins from Walsh Park and ends at North Ridgeway Avenue. That’s roughly 2.5 miles. You cannot possibly hike through the whole track, but you can use it to access other popular outdoor attractions in Chicago.

If you buy the CityPass for Chicago before visiting the city, you can walk across the 606 trail and get off at well-known tourist attractions such as Humboldt Park and Wicker Park.

    10. Lake Michigan Paddleboarding

Lake Michigan offers lots of ways to cruise through its blue waters. But, nothing matches paddleboarding when it comes to experiencing the ultimate outdoor thrill.

Especially if you visit during the summer, you’ll find the lake water refreshingly cool to beat the heat. You can dedicate an entire day from your itinerary to paddleboarding and enjoying the lake with your family.

Many places have paddleboards available for rent, including Monroe Harbor and North Avenue Beach. Some of these places also let you take paddleboarding classes before stepping into the water.

So, even if you’re apprehensive about going paddleboarding with your family, you can have a learning experience together and then set out to have fun. Remember, paddleboarding can be quite exhausting, especially when it’s windy. But, if you plan your vacation during summer, this is one of the best attractions in Chicago for nature lovers.

See Related: Is Chicago Safe for Travelers?

    11. Maggie Daley Park Rock Climbing

Rock climbing is one of the best attractions in Chicago for those who crave adventure.

Normally, you’d expect to find rock climbing options in national parks and rural areas. Surprisingly, you can do this activity inside the bustling city of Chicago in Maggie Daley Park.

Maggie Daley Park Rock Climbing

The park has a 40-foot outdoor climbing wall, which has around 19000 square feet of climbing space in total. The best part is that the park offers climbing options for beginners to high-level climbers. This means you can have fun climbing with your family without any security hazards.

Besides that, the climbing area has crash pads and efficient safety staff to avoid unpleasant accidents that spoil your enjoyment.

You can try out bouldering and top-rope climbing. At the same time, children and beginning climbers can try lead climbing. You can rent the equipment you need from the park itself, in case you didn’t bring your own. The park has high-quality rental equipment like helmets, shoes, and belay devices for about $30-$50.

     12. High-Speed Boat Cruises

There’s nothing like a high-speed cruise across the water to pump up your adrenaline levels. Speed boating is one of the best attractions in Chicago for visitors who love thrilling outdoor adventures.

You can take speedboat cruises lasting around 30 minutes to an hour, depending on the provider who arranges your tour.  Many cruises begin at Navy Pier and move through the Museum Campus, ending at the Magnificent Mile.

Those who want the ultimate thrill can take extreme boat rides that include sharp twists and complete 360-degree turns. On the other hand, if you want a laid-back, relaxing experience, you can go for a leisurely boat tour and enjoy the picturesque views of the city.

See Related: Thrifty Traveler Review

Final Words

Concluding my list of the best attractions in Chicago, I am sure you’re ready to pack your bags right away. However, the secret to spending the best vacation alone or with your family is effective planning.

Make sure you have a perfect itinerary mapped out. By doing that, you won’t end up wasting your days or missing out on the good stuff. Also, try to book tickets for the events and places you want to attend.

Most importantly, if you’re going for an outdoor adventure, you should have your safety and first-aid gear ready with you. This way, you can stay safe in case of an accident.

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