Oh, Chicago–the windy city is a fantastic place for some All-American fun. This booming Midwest metropolis hosts great parks and botanic gardens, modern architecture, some of the top museums in the country, fine dining with international favorites, and bumping nightlife that all comes together to form a slightly less hectic version of NYC. Famous for spectacular Broadway performances in the theaters, Chicago lights up with prime entertainment by night. See the skyscrapers reach great heights with the top two tallest buildings in the United States–the world famous, 108-story Willis (formerly Sears) Tower and the 98-story Trump International Hotel and Tower, which opened in 2009. Set sail on a scenic cruise out over Lake Michigan and look back at the sight of the Chicago’s vast panorama and towering skyline from the water. Attractions include Navy Pier, Shedd Aquarium, The Field Museum, Adler Planetarium, the Museum of Science and Industry, and the oldest free zoo in the country, Lincoln Park Zoo.

Be sure to check out our Insider’s Guide To Chicago With Emmy Award winner Lisa Lubin. I’ve also got a post with 33 fun facts about Chicago that you’re sure to love and get inspired! Save by getting the Chicago CityPass, which allows you to purchase a combination ticket to 5 Chicago attractions for 49% off their regular prices. Chicago is a 7 hour drive from Minneapolis (400 miles), 4½ hours from Detroit (280 miles), 6 hours from Columbus (260 miles) and 5 hours from St. Louis (300 miles).

Be sure to take a look at Cloud Gate, aka “The Bean.” It opened in 2006 as the centerpiece of Millennium Park.

Top 10 Attractions

1. One of the best aquariums in the nation, the John G. Shedd Aquarium contains 32,500 animals, 1,500 species and contains 5,000,000 gallons of water. See sea otters, beluga whales, pacific white-sided dolphins, North American river otters, sea lions, blacktip reef sharks, zebra sharks, rock hopper penguins, Magellanic Penguins and many, many more. The five permanent exhibits are Amazon Rising, Caribbean Reef, Waters of the World, the Oceanarium, and Wild Reef. The newest attraction is Fatasea, which is a show that premiered in 2009 with belugas, dolphins, penguins and sea lions. General admission (which does not include admission to some of the larger exhibits) is $8 for adults and $6 for children.

You can’t visit Chicago without a visit to the Shedd Aquarium!

2. Willis Tower became the new name of the Sears Tower in July 2009. The city skyline is obviously Chicago’s number one delicacy. You can see it from the the John Hancock Observatory or from the top of the Willis Tower. Built for approx. $150 million. Skydeck Chicago at Willis Tower is located on the 103rd floor. It can be reached by two elevators at the speed of 60 seconds. All glass boxes opened to the public on July 2, 2009. They allow you to look through the floor and can bear five tons of weight. Also considering visiting the John Hancock Center instead, Chicago’s 3rd largest building, which allows you to see 80 miles on a clear day. General admission is $18 for adults and $12 for children.

Fun Fact: This tower did not turn out to be as successful as was hoped. It stood half-vacant for over a decade! Sears vacated the building, which had been sold numerous times, by 1995. This is such a sad story, especially for Sears & Roebuck who lost so much money on this investment. I’m assuming this story is why this is the tallest building in the U.S. to date. Nothing could impress you more than a look at this spectacular skyline.

 3. Navy Pier receives 8.6 million visitors a year making it the tenth most visited attraction in the US. Navy Pier is a 3,300-foot long pier that was built in 1916 on the Chicago shoreline of Lake Michigan. Attractions: Pier Park is home to the Navy Pier Ferris Wheel, standing 150 feet high and offering 7-minute rides in the 40 gondolas that each seat up to six passengers, with views of the Chicago skyline, the Musical Carousel featuring 36 hand-painted animals, the Wave Swinger, with 48 seats that let you swing out over the water, an 18 Hole Miniature Golf Course, Remote Control Boats, and the Light Tower Ride, a 13 foot hopper. Chicago Children’s Museum was established in 1982. Permanent exhibits include Play It Safe, Kraft Artabounds Studio, BIG Backyard, Dinosaur Expedition, Inventing Lab, Kids on the Fly, Kids Town, Kovler Family Climbing Schooner, My Museum, Skyline, Treehouse Trails, and WaterWays. Admission is $10 for adults and children, yet free if you come on Thursday evenings from 5-8.

Amazing Chicago’s Funhouse Maze is a 4,000 sq. ft. maze that’s full of fun for everyone. The Navy Pier AeroBallon takes you high above Chicago, giving you a view like you’ve never seen before. Transporter FX lets you chose your thrill level when taking a high speed motion thrill ride to the Antartica, to the Moon, or to Wild Africa, Fly into Combat, or Race in the Grand Prix. Admission is $6. Bike and Roll Chicago offers bikes and skates for rent by the hour, day or week. Segway Experience of Chicago offers two-hour tours seven days a week beginning at 11am-May-September. Smith Museum of Stained Glass Windows opened in February 2000 and houses a permanent display of 150 stained glass windows in an 800-ft.-long series of galleries It’s the first museum in the United States dedicated to stained glass windows and best of all admission is free. Numerous cruises, dining and shopping options and so much more are all available at Navy Pier.

Ride the huge ferris wheel on Navy Pier… well unless you’re scared of heights. Once you get off, enjoy the creperie next door!

4. Adler Planetarium & Astronomy Museum was built in 1930 is a part of Chicago’s Museum Campus along with the Shedd Aquarium and the Field Museum of Natural History. It was the first planetarium built in the Western Hemisphere and is the oldest in existence today. Current temporary exhibits are Telescopes: Through the Looking Glass, through December 2010, and From Earth to the Universe, through June 2010. Permanent Exhibits are Bringing the Heavens to Earth, CyberSpace, From The Night Sky To The Big Bang, Our Solar System, Shoot for the Moon Exhibition, Space Visualization Laboratory, and Universe In Your Hands. Shows: 3-D Vision: Imaging the Universe, One World, One Sky: Big Bird’s Adventure, IBEX: Search for the Edge of the Solar System, 3D Universe: A Symphony, Cosmic Collisions, Skywatchers of Africa, and Night Sky Live. Get free admission if you come on Charter One Discount Days. General admission is $12 for adults and $8 for children.

5. The Field Museum of Natural History was founded in 1893 and currently has many popular exhibits like “Sue,” the largest and most complete Tyrannosaurus currently known, a set of human cultural anthropology exhibits, including artifacts from ancient Egypt, the Pacific Northwest and Tibet, a large and diverse taxidermy collection, featuring many large animals, including two prized African elephants and the Lions of Tsavo, featured in the 1996 movie “The Ghost and the Darkness”. A large collection of dinosaurs in the Evolving Planet exhibit (formerly Life Over Time). A large collection of Native American artifacts. The main exhibit with these artifacts reopened as Ancient Americas in March 2007. General admission is $15 for adults and $10 for children.

6. Lincoln Park Zoo opened in 1868 and is located on 35 acres with almost 1,250 animals. It’s free of charge and it receives over 3 million annual visitors, making it the second most-visited zoo in America. Animals include Western Lowland Gorillas, Chimpanzees, Red Kangaroos, Snow Leopards, Red Pandas, Polar Bears, Gray Seals, North American river otters, Baringo giraffes, Dwarf Crocodiles, and so many more. Exhibits and Animal Houses: Regenstein African, McCormick Bear Habitat, Kovler Penguin and Seabird House, Helen Brach Primate House, Kovler Lion House, Kovler Sea Lion Pool, Pritzker Family Children’s Zoo, Regenstein Small Mammal-Reptile House and The Nature Boardwalk at Lincoln Park Zoo. Attractions at the zoo are The AT&T Endangered Species Carousel, which features 48 wooden animals and two chariots and can accommodate up to 50 riders. The LP Zoo Express Train is a children’s train (suggested ages 3-12 years old). It’s the oldest free public zoo in the country.

7. Art Institute of Chicago – The 5th most visited art museum in America is home to one of the world’s largest collections of Monet paintings, as well as big names like Picasso, Matisse, de Kooning and Pollock. Famous paintings include Grant Wood’s American Gothic, Seurat’s Sunday Afternoon on the Island of La Grande Jatte. And if those names don’t sound familiar, then see if any of these pictures look familiar! Japanese ukiyo-e prints, ancient Egyptian bronzes, Greek vases, 19th-century British photography and modern American textiles are some their biggest attractions. It’s located in Grant Park and it’s currently the second largest art museum in America. Admission is $18 for adults and $12 for seniors and students.

8. Museum of Science and Industry – Head to Hyde Park to explore this incredible museum, which features over 2,000 exhibits. See the U-505, a German submarine that was captured in 1944 and brings home the claustrophobic reality of underwater naval life. The full-scale Coal Mine dates back to 1934 and incorporates modern mining techniques, offering a simulated trip down into a dark, mysterious mine. The “All Aboard the Silver Streak” exhibit features a refurbished Burlington Pioneer Zephyr train with onboard interactive exhibits and “Take Flight” is an aviation exhibit featuring a full-size 727 airplane. It’s a good distance from the other attractions, but it can be reached by bus or the Metra Electric train, or of course by car or taxi. Admission is $15 for adults, $14 for seniors and $10 for children.

9. Frank Lloyd Wright Home and Studio – Go on a guided tour of the place that America’s most-famous architect once called home, for the first 20 years of his career. It’s where he designed and executed more than 130 of 430 completed buildings. Wright remodeled the house constantly until 1911, when he moved out. It’s interesting to see how he customized this home for his personal taste and needs, such as a barrel-vaulted children’s playroom and a studio with an octagonal balcony suspended by chains. Admission is $15 for adults and $12 for seniors and children.

10. Six Flags Great America is located about an hour outside of the city center but it is always a fun option for those looking for big thrills or family fun. They have over 100 rides and attractions, including 10 roller coasters. Children will enjoy the Looney Tunes National Park section, the famous double-decker carousel and the old-fashioned bumper cars. While here, also visit their Hurricane Harbor water park, which features a massive wave pool. Admission is $55 for adults and $35 for children.

Looking for even more inspiration? If you haven’t already, be sure to check out my post on 33 Fun Facts About Chicago!

See a performance at the Chicago Theater… or simply visit to get your photo taken in front of this world renowned landmark!

Restaurants

Ralph Lauren Restaurant – The RL restaurant opened in 1999 and has become a favorite among many celebrities – including Chicago “native” Oprah Winfrey, who frequents the place! She brought Justin Bieber here for her interview with him in 2012 and he seemed to like it a lot too!  It’s located right next door to the world’s largest flagship Polo store. Many dishes are prepared table side in this classic Chicago eatery. Like just about any restaurant, most entrees are cheaper at lunch. Those coming for lunch may want to try the Polo Club sandwich for $15.75, while those coming for dinner may want to splurge on the Garlic-Parsley Roasted Lamb for $47.75. The dress code is smart business casual and valet parking is available after 5:00 PM.

Ed Debevic’s – Every kid’s fantasy! Servers are dressed up as characters with an overly joyous attitude! They even start randomly dancing on the counters, talk about atmosphere! They serve hot dogs, hamburgers, homemade chili, fries with gravy or cheese, milkshakes, and delicious sundaes. Chicago’s only retro themed diner opened in 1984 and has been a huge hit ever since.

You can’t visit “Chi Town” without getting their classic deep dish pizza. 

Margaritaville – Named after Jimmy Buffett’s famous 1977 song, Margaritaville, redefines the meaning of the laid back American lifestyle. Sip on a Pina Colada and chill by the bay, here at this delicious restaurant. Don’t forget to pick up Jimmy Buffet themed merchandise on the way out.

Tommy Gun’s Garage – Chicago’s longest running audience interactive dinner show has been around since 1987. It was featured on The Food Network’s “World’s Weirdest Restaurants.” It is given 4.5 stars on TripAdvisor and it received a 2013 Certificate of Excellence. They describe it as an “Audience Interactive “Speakeasy” that offers a musical comedy review wit da gangsters, da flappers and YOU!!!!! (uh, dat’s audience participation). After a delicious sit-down dinner, join “Vito”, “Gloves”,  and da “gangsters” and da “flappers” for non-stop comedy and dangerous fun.  You will be transported back to da 1920’s complete wit da boss’s 1928 Model “A” Ford, Roaring Twenties music and memorabilia from da Twenties.” Dinner shows typically cost between $60 – $70 per person. Coupons may be found on their website.

Rainforest Cafe – Step into this indoor jungle and discover one of the most realistic indoor rain forests ever created, complete with cascading waterfalls, lush vegetation, tropical rainstorms, beautiful aquariums, trumpeting elephants and wild animatronic gorillas, jaguars, and elephants. A “thunderstorm” goes off every now and then, where the ”animals” go wild and thunder and lightning appear to sound off in a dramatic yet exciting experience. The menu includes a wide variety of options, including pastas, seafood, salads, sandwiches and pizzas. Order their “volcano” sundae and they start yelling “volcano” and make quite a spectacle! Pick up a souvenir on the way out at their large, iconic gift shop. Located about eight blocks from Trump Tower.

The Cheesecake Factory – Since first opening in Beverly Hills in 1978, these restaurants have become well known for their fun atmosphere, huge portions and more than 200 menu selections to choose from. They offer 50 cheesecakes and specialty desserts, with some that are only offered seasonally. These include: Key lime cheesecake, Chocolate Chip Cookie – Dough cheesecake, pumpkin cheesecake (available from October – holidays), Pineapple Upside-Down Cheesecake, and after thanksgiving they even have a peppermint Bark Cheesecake! This location is located on the ground level of the John Hancock Building.

Hard Rock Cafe – They have celebrated over 25 years at the corner of Clark and Ontario, in the heart of Chicago’s River North neighborhood. Located just 5 blocks west of Michigan Avenue, the Hard Rock Cafe has something special for all. Whether you need a Hickory-Smoked Pulled-Pork sandwich after shopping on the Magnificent Mile or a Rockarita after the theater, you’ll find a wide variety of Legendary Cuisine.

Bubba Gump Shrimp Co. – Owned by the people who own Rainforest Cafe. Since 1996, Bubba Gump Shrimp Co. has been entertaining guests with a charming down-home style that’s a hit with eaters around the globe. Their menu offers a number of items for the shrimp lover in all of us. Boasting creative seafood dishes inspired straight from the movie Forrest Gump and a fun family atmosphere, Bubba Gump Shrimp Co. will have you running to the nearest location you can find! Although that movie came out around 20 years ago, this popular restaurant never fails to delight.

Sitting in a glass box atop Willis Tower is sure to scare you enough to work up an appetite!

American Girl Cafe – Anyone with a young daughter or grand daughter will have to bring their girl here to this full-service restaurant! Brunch is $19 per person, lunch is $22, afternoon tea is $19 and dinner is $23. Dinner is only offered at select times. Let your girl shop next door for dolls, t-shirts, posters, and all things girly!

Weiner’s Circle & Dick’s Last Resort – I know, I know… but don’t let the names scare you off! Dick’s even has an “I Love Dick’s” bumper sticker on their website.. so yeah, these places aren’t really meant for kids! These classic eateries are notorious for their extremely rude service. This is the place where customers get to talk back and cuss up a storm at their arrogant waiter.

Alinea – This place was not meant for your average tourist. But those looking for something truly out of the ordinary will love this extraordinary restaurant that charges $210 for it’s 18-course tasting menu. The selection includes: snow, urchin, venison, tofu, brie, and so many other unique favorites!

Medieval Times Dinner Theater – is a family dinner theater featuring staged medieval-style games, sword-fighting, and jousting performed by a cast of 75 actors and 20 horses. It is housed in a replica 11th-century castle.

Shopping

Woodfield Mall – Located just outside of Chicago, Woodfield is the number one tourist destination in the State of Illinois. Its name pays posthumous tribute to two of the greatest retailers of all time: General Robert E. Wood of Sears fame and the legendary Marshall Field. Many of the specialty stores are the largest of their kind in the U.S., and Woodfield is often used to test new store design and marketing concept, such as how the 2004 opening and nationwide debut of RUEHL 925 by Abercrombie & Fitch made its premiere here. Its trademark stainless-steel sculptures were fashioned by artist Robert Engman. Stock up on your Cubs sports apparel and novelties at the Cubs Clubhouse or just let the kids play at their indoor mini golf facility called Glow Golf or at Yu Kids Island, a fun indoor play facility! It was featured on our list of America’s Largest Malls.

The LEGO Store – As featured on our list of the 9 Coolest Toy Stores in America, The LEGO Store is more than just a place to find the latest and greatest LEGO sets—it’s an experience filled with life-sized statues and mini architecture from Willis Tower to the White House. There is a designated play area so kids can have a hands-on experience. Inside you will see statues of favorite movies and characters from Star Wars to Disney Princesses. These LEGO sets will not disappoint or you can even fill up on an assorted tub—the classic way to go! To see the LEGO Store, just stop into Water Tower Place at 835 N Michigan Avenue on the Mag Mile in Chicago. It’s open Monday through Saturday from 10 am to 9 pm and Sundays from 11 am to 6 pm.

Transportation

Coming Soon!

Hotels

2.5 Star- The Willows (Avg. price $127-$245) Located within 1.5 miles of Lincoln Park Zoo and Wrigley Field, this hotel remains fun yet affordable. A continental breakfast is included.

Key Lime Cove – This indoor water park resort is located just three blocks away from Six Flags Great America and it is billed as “the official resort of this Six Flags.” It is located about an hour outside of Chicago in Gurnee, Illinois.

Transportation

The O’Hare International Airport is by far the largest airport in Chicago and it is the second busiest airport in the world (right after Atlanta, GA).

*Those visiting or considering moving to the Wicker Park/Buckhead area will want to check out our complete review of that area.

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