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Chicago is a city loved by many and for so many reasons. But what if you have never been there or have only been for quick work trips? How would you know where to go and what to see? You came to the right place! In most of our U.S. travel articles we boast that buying a City Pass is one of the smartest things you can do when visiting a new city. Well Chicago is no different, savings abound when purchasing this pass. At least 6 of the attractions and museums listed below are included in the City Pass purchase price and in addition to getting a deal, most places have expedited lines for City Pass holders, potentially saving you hours of waiting.

  1. Lake Michigan – You may have seen this from other sides or even other states but there is nothing quite like the north shore of Lake Michigan in Chicago. There’s everything from beach volleyball to paddle boarding and seadoo rentals. It’s always busy when the weather is nice. Lake Shore Drive.
  2. Original Playboy Mansion – A cool iconic thing to swing by and see. It’s on a beautiful tree lined street and was smaller than I thought it would be. But it was none-the-less a gorgeous home. It’s interesting to think that Hef started the infamous Playboy brand there so many years ago . 1340 N. State Parkway.
  3. Adler Planetarium – If learning about space is something that interests you, there are enough facts to keep you busy visiting this museum for probably around 2-3 hours depending on your interest level. 1300 S. Lake Shore Drive.
  4. Shedd Aquarium – Shedd is somewhere you could spend all day, from petting sting ray to watching various different aquatic shows. This is a definite pleaser for people of all ages. 1200 S. Lake Shore Drive.
  5. Biograph Theater – This historic monument is a must see, once a movie theater but now the home to many live performances. The Biograph became a notable place in 1934 when gangster and bank robber, Robert Dillinger was shot to death right out front of the theater by FBI agents after completing a fleet of 24 bank robberies, 4 police station robberies, and escaping prison twice. Although he was never convicted they say he shot and killed a police officer as well. 2433 North Lincoln Avenue. Near Lincoln Park.
  6. Museum of Science and Industry – This is probably the most impressive, spectacular museum we have visited to date. Chalked full of scientific demonstrations of natural occurrences from hurricane simulations, to chicks hatching from their shells to still born babies preserved to show the growth stages by week. This museum is huge and to truly explore everything you just may need more than a day. 5700 S. Lake Shore Drive.
  7. Wrigley Field – Cubs games are like no other major league baseball game. Chicagoans fill the stadium to the brim. Good luck getting last minute seats to these lively games. Definitely plan in advance as they tend to be sold out at just about every game.1060 W. Addison St.
  8. Field Museum – The Field Museum is very much like visiting the Natural History Museum in Los Angeles or New York. There is lots to do at this museum including but not limited to viewing various fossils including that of a T-Rex, stopping into the DNA Discover Center and learning about ancient Egypt. 1400 S. Lake Shore Drive.
  9. Magnificent Mile – The Michigan Avenue District of Chicago is filled with wonders old and new. From all of the top shopping brands like Chanel & Yves Saint Laurent to some amazing restaurants. You may want to stop into some of the hotels on Magnificent Mile as well. The Blackstone Hotel to mention one, is notable for hosting every U.S. President from Taft through Carter. If you like architecture, check out the Bloomingdale’s Medinah Home Store, it’s 105 years old! It has a beautiful detailed façade.  625 N. Michigan Avenue.
  10. Chicago Theater – There is always a full line up of shows to be seen at the Chicago Theater. However, if you are not seeing a show, just walking by the front of the theater with the Chicago marquee happily blinking and lighting up North State Street is definitely worthy of a photo opp. 175 N. State Street.
  11. Skydeck at Sears Tower (Willis Tower) – Skydeck has one of the most beautiful views from a high, especially because you can see Lake Michigan. Another special feature of Skydeck is the glass boxes that extend out 4.3 feet from the side of Skydeck and are 1,353 feet in the air! If you don’t get queasy from heights this is a must do. 233 S. Wacker Drive.
  12. Navy Pier– This ended up being a place we went to twice. The first time to shop and eat during the day and then back again for the spectacular picture at the top of this article. Chicago has one of the most beautiful skylines and you just happen to be able to see it best from the Ferris Wheel on Navy Pier. 600 E. Grand Ave.
  13. Millennium Park – This is a park beyond parks. Home to one of the largest Jazz festivals in the U.S, Millennium Park has hosted various different artists at its Jay Pritzker Pavilion. The pavilion itself can hold 11,000 people. There are quite a few sculptures and gardens throughout the park, including the Crown Fountain, an interactive work of art composed of a black granite reflecting pool. Weather permitting this fountain puts on a show every 5 mins. Be sure to check the parks website below for a schedule of fun things to do. 201 E. Randolph Street.
  14. The Bean (Cloud Gate) – The bean is a world famous landmark, having been shown in numerous films and remaining one of the most photographed works of art in the world. It is center piece at the AT&T Plaza entrance to Millennium Park. 201 E. Randolph Street.
  15. Ed Debevic’s – This remains a personal favorite as I can remember frequenting the Los Angeles location as a kid. Unfortunately, the Chicago location is currently closed and moving to an undisclosed location. The music, the food, the dancing and the manners are definitely worth a visit when it reopens downtown. Keep an eye on the website below for their new address if you’d like a thankless meal where they eat the fries right off of your plate and happily kick you out while dancing and singing to all your Doo-wop favorites. No Address right now.
  16. Eataly – A culinary delight for all foodies! Everything they make and serve prepared is sold in a market style fashion. Italian dishes galore from fresh buratta to pasta alla carbonara and everything in between, including some of the most delectable gelato. Enjoy the second floor restaurant Birreria for a glass of wine or cruise through the market trying tiny bits of this and that. 43 East Ohio Street.
  17. Gold Coast – The Gold Coast is Chicago’s historic district and grew in size and popularity after the Great Chicago Fire in 1871. The district was added to the National Register of Historic Places in 1978. It has many mansions, apartment high rises and row-houses and has become the second most affluent neighborhood in America behind Manhattan’s Upper East Side. Make sure to check out Astor Street District and the James Charnley House. Expands from North Ave to Lake Shore Drive.
  18. Chicago River– With a length of 156 miles, the river passes through the Chicago Loop and can’t be missed with its bridged canals and water side restaurants. Head to the South Branch at Wolf Point for an amazing photo opportunity. Between Wacker Drive and Roosevelt Rd. is perhaps the most popular area within the loop to view the river.
  19. Golden Triangle – The Golden Triangle is an area not just a restaurant in the Golden Triangle as you may find if you Google. There are many restaurants, shops, hotels and bars in the triangle shaped area and dead center is a small park with the quaintest coffee shop. It’s a very nice quiet place to sit and people watch or enjoy a fabulous meal with friends. Locals call it Viagra Triangle, I’ll let you determine why it’s called that. I honestly didn’t see why. 330 N. Clark St.
  20. 360 Chicago – This is an observation deck that offers 360 degree views of Chicago 1000 feet about Magnificent Mile. You can dine in one of the cities most scenic views or for the brave you can hop on the ride Tilt which leans you over the side of the John Hancock Tower that 360 Chicago is placed atop of. 875 N. Michigan Avenue. 94th Floor.
  21. Art Institute of Chicago – A collaboration of worldly exhibits and chalked full of art pieces from Matisse to Picasso. For the art enthusiast an entire day could be spent here visiting the collections and exhibitions. 111 S Michigan Ave.

We hope you enjoyed our tour through the 21 Must Sees in Chicago. Many more cities to come. Sign up for our daily highlights and travel tips to be sent to your email by clicking the ‘follow’ button at the bottom of the page.