What to SEE in Chicago
Chicago is a city filled with iconic art and attractions, so many that one visit will not be enough! There are literally hundreds of things to do on any given day. I am going to give you my top 20, with some Jac Of All Travels tips thrown in.
Stay til the end and I will fill you in on how to get a discounted pass to explore some of your favorites! (Because who doesn’t love a deal?!)
Be sure to look out for tips like this throughout:
*JOAT tip: Be sure to check online for discounted tickets, sites like Groupon often have good deals
1) River Boat Architecture Tour
One thing that is an absolute MUST when you visit the Windy City is the Chicago River Boat Architecture Tour. Immerse yourself in the rich history of the iconic architecture that makes up this beautiful city. Expert guides share fascinating stories as they take you on an informative, but light-hearted, open-air ferry ride down the Chicago River passed the city’s most iconic landmarks and skyscrapers. Opt for a relaxing day cruise or venture out in the evening as the buildings begin to twinkle against a dusky backdrop. There are many boat tours to choose from, they will all generally have a bar and some serve light food. Prices generally range from $37-50 for adults or $19-$25 for kids.
I hopped aboard the Shoreline Sightseeing cruise (twice!) and found the guides to be witty and entertaining, in a very informative way.
Shoreline Sightseeing Tickets: $37/$43 adults; $19/$24 children
*JOAT tip: Check online for discounted tickets, sites like Groupon often have good deals
Address: Shoreline Sightseeing- 600 E. Grand Ave, Chicago, IL 60611
2) Navy Pier
There’s plenty to do on the pier! Consider it the epicenter of fun, there’s something for everyone here. While this may be considered very touristy, you’ll definitely need to visit at least once! Take a spin in the 15-story ferris wheel for magical views of Lake Michigan and the stunning city or stay on ground and immerse yourself in shopping, games, rides, tours, and more! The pier offers an IMAX theater, Children’s museum, funhouse, a beer garden, a botanical garden, just to name a few-the options are as endless as the eateries!
*FREE to visit
After hours of excitement, you’ll be famished so visit the updated food court where you can savor in some soul food at Big City Chicken or perhaps indulge a cheesy classic deep dish pizza at Giordano’s. O-M-G that cheese! (Did you know you can ship frozen pizzas home?! Highly recommended 😉 Lol)
Address: 600 E. Grand Ave, Chicago, IL 60611
3) Chicago Riverwalk
If people watching is your thing, this is the place to go! Referred to as the city’s “Second Lakefront,” the Riverwalk showcases a variety of restaurants, museums, memorials, and scenic views for endless photo ops. From the Riverwalk you can hop on a boat or jump in a kayak and explore the canals for a more adventurous view of downtown.
*FREE to visit
JOAT Tip: To all my brunch lovin’ blog readers (because who doesn’t love a good brunch?!)- Do yourself a favor and check out River Roast’s Brews & Blues Brunch featuring a live Blues band from 12pm-3pm every day. James Beard award-winning Chef Tony Mantuano takes roasting to a whole different level with his exceptional menu in an atmosphere that remains laid-back and charming. Make sure to come hungry! Their Bloody Mary will cure any hangover and is accompanied by a stack of snacks! If you enjoy brunch too much you might end up at their pretty awesome happy hour (3pm-5pm), currently called “Champagne & Chicken”. Count me in!
4) Grant Park
Grant Park is a 320-acre park located in the Loop district that wraps Chicago’s shoreline and is home to many of its most famous attractions, iconic landmarks and biggest events. You will undoubtably spend some time here on any visit to Chi-town! Sprawling along Lake Michigan, this park’s most notable features are Millennium Park, Buckingham Fountain, the Art Institute of Chicago, Shedd Aquarium and Adler Planetarium. Buckingham Fountain, one of the largest fountains in the world, displays a spectacular 20 minute water show on the hour of every hour from May until October. Grant Park also notably hosts the Chicago Marathon and the Lollapalooza music festival.
*FREE to visit
5) Millennium Park
No visit to Chicago is compete (or even possible?) without a visit to Millennium Park. Made up of 25-acres of beautiful landscape and gardens decorated with iconic public art and surrounded by world famous skyscrapers, this park encompasses everything from cultural exhibits, music events, art installations and much more! Anish Kappor’s first U.S. public sculpture, Cloud Gate (aka The Bean) is definitely one of Chicago’s most iconic landmarks and selfie seeking insta-worthy works of art you won’t want to miss! Fun fact: It took 168 steel plates seamed perfectly together and shined to perfection to make this glistening gate.
Also home of the Jay Pritzker Pavilion which showcases many concerts and film screenings all year round but most notably hosts Chicago’s Summer Film Series and Summer Music Series. And in winter months, you can take a spin on the McCormick Tribune Ice Rink under the famous Bean.
Crown Fountain is a larger-than-life video installation created by conceptual artist Jaume Plensa in 2004. Perfect for cooling off on those hot summer days, these two 50-foot video fountains featuring faces of Chicagoans spout water from their “lips” into a reflection pool.
For you adventure types, Maggie Daley Park adorns two 40-foot rock-climbing walls that you can scale to the top for FREE. Once at the top, take a second to savor in the stunning view of Lake Michigan and Chicago’s famous skyline.
5-acre botanical beauty Laurie Garden decorates Millennium Park and makes for a tranquil hideaway amongst the bustling city.
*FREE to visit
JOAT tip: Want to grab a trendy cocktail and a great view? Cindy’s offers a hip atmosphere with an incredible rooftop bar that overlooks Millennium Park and The Bean, perfect for people watching. Be sure to make a reservation if you want to stay for dinner!
Fun Fact: It is inevitable that hundreds of people will be photo bombing your Bean pictures, but on my first trip to Chicago to visit my bestie (and fellow photographer), we were granted special private access to The Bean after dark. Using our powers of persuasion and our undeniable charm (wink wink), we somehow managed to get a few minutes alone with Cloud Gate. What a unique and exciting experience, especially for two photographers!
6) Magnificent Mile
Chicago’s premier commercial district is known as the Magnificent Mile (or Mag Mile) and spans from the Michigan Avenue Bridge to Oak Street Beach. This vibrant area houses upscale boutiques, trendy restaurants and several historical sites. In 1871, the great Chicago fire set the city ablaze but amazingly spared the Water Tower and Pumping Station which still stand as reminders of that fateful day. Other landmarks include the neo-Gothic Tribune Tower, the terracotta Wrigley Building skyscraper and the 100-story John Hancock Center.
*FREE to visit
JOAT Tip: For the most amazing panoramic city views, stop at the top of the cock! The former John Hancock building that is! But now simply known as 875 North Michigan Avenue (whomp whomp). Ride up to the 96th floor for a fancy drink and a fantastic view at the Signature Lounge or experience fine dining at its best in The Signature Room.
7) Willis Tower (Skydeck)
Standing 110 stories high, the 1,450-foot Willis Tower (aka Sears Tower) is the second tallest in USA, behind New York’s One World Trade Center. Watch for ear popping as you quickly ascend, but listen up while the informative elevator spouts off facts as you fly passed the heights of the Eiffel Tower and Statue of Liberty.
Are you brave enough to stand on The Ledge? The Skydeck in the Willis Tower is located on the 103rd floor with an elevation of 1,353 feet and hosts the highest observation deck in the U.S. However the most thrilling part of this attraction is not the panoramic view from its large windows, but from four retractable all glass balcony that extend 4.3 feet out from the building and suspends visitors over South Wacker Avenue. On a clear day that view can span over four states! There will probably be a line (several of them) to get one of the most unforgettable selfie shots, but it may be worth the wait for these spectacular city views (if not, opt for a Fast Pass to surpass the lines).
Ticket Prices: $25 for adults, $17 for kids under 12
JOAT tip: Don’t be alarmed by the stream of tourists that insist on jumping up and down in the box for photo ops (guilty), that glass is THICK and holds up to 5 tons. Just leave your elephant at home.
8) 360 Chicago Observation Deck
(formerly John Hancock Observatory)
In a rivaling observation deck across town, take the speedy elevators (complete with witty commentary) to the 94th floor where you’ll be greeted with 360 degree views of Chicago’s skyline and Lake Michigan. Hold on to your handrails kids, the 360 Chicago Observation Deck is also home to TILT, a moving platform with windows that literally tilt out 1000 feet above the Magnificent Mile for a truly exhilarating experience (extra $) and unique view.
Ticket Prices: $25 for adults, $15 for kids ages 3-11
TILT Price: $8
50% off for Chicago residents
JOAT tip: There’s a bar & cafe at this one! Complete with stunning city views! And usually shorter lines than at the Skydeck, but keep in mind TILT is extra $$.
9) Shedd Aquarium
An impressive and colorful fish tank greets you as you enter one of the largest aquarium’s in the world! Immersed in the 5 million gallon aquarium, you’ll find 3200 animals made up of about 1500 different species of fishes, reptiles, amphibians, birds and mammals from waters around the world. Spend the whole day or just a couple hours marveling at the beluga whales or shrieking as you stroke the slimy stingrays (eek!).
General admission: Adult $39.95, child (3-11) $29.95
50% off for Chicago residents
10) Adler Planetarium
Seeing the city might be cool, but to see what is above the city is a whole new perspective Established in 1930 as the first planetarium in the United States, this museum is dedicated to the study of astrology and astrophysics and sits in the Museum Campus section of Chicago which also houses Shedd Aquarium and The Field House. This makes it easy to do a museum day and experience each of them.
Adler Planetarium’s latest hit show, Skywatch Live, gives you the chance to observe a live view of the ever-changing sky above Chicago, making it a different show every day! You’ll navigate through the stars and experience just how vast and interesting the universe really is. With several theaters and many hands-on exhibits (suitable for any age), there’s enough exciting entertainment for hours. For locals, there are neighborhood skywatching parties and well organized youth programs for the kiddies.
JOAT Tip: You get the best view of the Chicago skyline from here! So make sure to wander outside to the waterfront.
General admission: Adult $19*, child $8*
*Shows and Atwood Sphere additional $
11) The Art Institute of Chicago
Chicago boasts one of the top 10 museums in the world and home to one of the largest exhibitions of Impressionist and Post-impressionist art. Travel through the centuries of fascinating art from around the world including iconic works such as Georges Seurat’s A Sunday on La Grande Jatte and Pablo Picasso’s The Old Guitarist
Ticket Prices: $25/adults; $19/Seniors, Students, Teens; FREE for children under age 13
Chicago Residents: $22/adults; $16/Seniors, Students, Teens; FREE for children under age 13
12) Museum of Science and Industry
You’ll need all day to explore one of the largest and coolest museums in the world, MSI is filled with unique experiences to stimulate your mind and inspire creativity. There are so many fascinating exhibits including the interactive Coal Mine, full size replicas of the Apollo 8 command module and a diesel-electric train (amongst others!)*. If that’s not enough to interest you-whip up the winds as you manipulate a 40-foot tornado or climb aboard a real German submarine*. The new Giant Dome Theater will leave you awestruck as you travel the globe from your seat through a colorful 5-story state-of-the-art laser projection system.
Ticket Prices: Adult: $21.95; Child $12.95
*Some experiences require add’l fee
13) Wrigley Field
Grab the fam and take them out to the ballgame! This major league ballpark is the legendary home to the Chicago Cubs (World Series Champs 2016, 1908, 1907), set charmingly off a residential neighborhood. Cheer on the Cubs, chug a cold beer and chow down on a Chicago Dog-doesn’t get better than that! Not a baseball fan? Wrigley Field offers an intriguing and informative tour highlighting the history of the Cubs as they take you around the stadium, through locker rooms and dugout, and stop for a photo op against the famous ivy covered outfield wall. It is truly a fun and interesting experience, even for un-sporty people like me!
Ticket Prices: Non-gameday Ivy Tours are $35 per person, with children under 2 being free
Buy Ivy Tour Tickets HERE
14) Lincoln Park Zoo
Founded in 1868 and one of the oldest zoos in America, this 35-acre zoo houses more than 200 rare and endangered species.
*FREE to visit
JOAT tip: Wander down the Nature Boardwalk to the bridge for spectacular city views just passed the South Pond.
15) Chicago Cultural Center
The largest Tiffany dome in the world decorates this municipal cultural center, first opened as a public library in 1897, it now gives way to free cultural exhibits and performances throughout the year.
*FREE to visit
16) The Chicago Theater
Catch a Broadway show at the legendary Chicago Theater or if that’s not your thing check out one of their many concerts, comedy, musicals or performances!
At the very least, grab your photo op in front of the famous sign…and DO NOT just run in the middle of the busy city street at night to do so…**ahem**
17) SECOND CITY
Love to laugh? Second City’s sketch comedy and improv-based sketch comedy will leave you with tears streaming down your face. Legendary alumni include Tina Fey, Chris Farley and Bill Murray.
18) Garfield Park Conservatory
This magnificent botanical conservatory flourishes with plant species from around the world, all encompassed in 2 lush acres indoors and 10 acres of gorgeous greenery outside.
*FREE to visit
19) Lakefront Trail
With the serene waters of Lake Michigan on one side and Chicago’s striking skyscrapers on the other, Lakefront Trail offers a paved path that runs 18.5 miles along the shoreline perfect for biking, blading or just a stroll.
20) Hike the 606
Formerly called the Bloomingdale Line, now called The Bloomingdale Trail, this once abandoned rail line is now 2.7 miles of a multi-use recreational trail decorated with lush greens and street art. Mocking NYC’s High Line, it makes for a scenic jog, cycle or stroll above Chicago’s northwest neighborhoods.
*FREE to visit
Too many sites to choose from?
Save money and skate by the lines when you get a Chicago City Pass. For $108 (adult)/$89 (child), this fast pass covers admission to Shedd Aquarium, Field Museum, Adler Planetarium or the Art Institute, Museum of Science and Industry or 360 Chicago (valid for nine days).
Another option is a Go Chicago Explorer Pass for $81-$121.50(adult)/$52-$81(child) which includes admission to 3, 4, or 5 attractions/tours/activities of your choice (valid for 30 days). This pass saves you up to 42% off regular ticket prices.
*Please note prices were valid at time of original publishing and are subject to change