Updated: May 21, 2015

Top 10 Things to See and Do in Chicago:

Chicago, also known as the "Windy City", has lots of famous spot to visit if you are a tourist. To come up with a top ten list is not that hard given all the excellent entertainment options in town. Whether you want views, rooftop bars, ballgames, or the finest restaurants, Chicago offers up all that and more. I have tried to compile a short list of the Top 10 highlights to the city - places and things that no one should miss out on. We have also added a few bonus things to the list just because we know that some people will have more time on their vacations.


Chicago Sightseeing: What to see in Chicago:

1. Get a view of the city from a tall building. One of the things that I like to do in any city is to get up as high as possible and see the sights. In Chicago you have 2 options - check out Willis (Sears) Tower or try the Hancock Observatory. The Willis Tower is the tallest building in the Western Hemisphere at 1450 feet The Skydeck is the perfect place to take in all that Chicago offers. The Ledge is a glass box that sticks out more than 4 feet with nothing below you but open space. It's open 365 days a years and admission is $17. On the other side of town stands the John Hancock Observatory which is just as cool as the Sears Tower, but gives you a slightly different viewpoint. Great for seeing Lake Michigan, Willis Tower, Chicago River, Magnificent Mile, Wrigley Park, and more. I've done both and recommend the Hancock building over Willis Tower. Either way, you get a great perspective on the city and excellent photo opportunities.

2. Walk the Loop. Besides the Magnificent Mile, most locals will tell you to walk the "Loop" if possible. It's a section of downtown that stretches from Lake St. south to Van Buren and from Wells to Wabash (running West to East). The L Train does a "loop" here so you can see some of it on the trains. It's an easy walk and you'll be amongst some tall buildings. Don't miss buildings like those found at 333 W. Wacker Drive - a triangular lot with a unique architectural design to fit. Chicago Board of Trade is near Jackson Blvd and N. Lasalle. Another stop should be at the Daley Plaza where you can see the Picasso Sculpture - located between Clark and Dearborn near W. Washington St. The "Loop" takes about 90 minutes to walk through and around. Recommended during business hours so you can see the ebb and flow of the city.

3. See Millenium Park and Grant Park. One of the best parts about Chicago is that it's literally right on Lake Michigan. The downtown parks like Millenium and Grant are what make this city so fun in the summer with events, music, and just getting out. We say start up towards the top of Millenium Park and make your way towards Grant Park. Perhaps the most famous spot is called Cloud Gate - a 110 ton elliptical scuplture that is made with stainless steel plates. Very impressive to see and worth a look. Some people call it the "giant bean". There is an ice rink in the winter at the McCormick and Tribune Plaza. When I was recently in town the Gourmet Food convention was in town and it took up a big portion of the Chase Promenade - it was closed to the public unless you had tickets. Check the website at http://explorechicago.org/city/en/millennium.html to see what will be going on in the park while you are in town. Another landmark is the Buckingham Fountain (from the show (Married with Children). Kids love watching it and on a nice day it's a great place to rest your feet. If you have the energy continue down to Grant Park which eventually leads you to Sheed Aquarium, Field Museum and Soldier Field (home of the Chicago Bears).

4. Take a Water Taxi on the Chicago River. When a city has a river that runs through it (Chicago River) and a massive lake next to it (Lake Michigan), the water is perhaps the best vantage point when exploring. Water taxis in Chicago are a great way to get around and see the buildings from water level. Get out to Navy Pier on a water taxi or go on a dinner cruise out on the lake. The 3 spots to catch or get off a taxi are at Navy Pier, Michigan Ave stop, and the Madison Street stop. Chicagowatertaxi.com/ is a good website to start with, find out about fares (starting at $2), get schedules and get a route map. We took a water taxi service provided by Shoreline Sightseeing - started at the Michigan Avenue Bridge. When the weather is nice, there's no better way to see the city. The Architectural cruises offered by this company are highly recommended.

5. Ride the L Train. The Chicago Transit Authority (CTA) has made travel throughout the city fairly easy. There are colored 'L' trains that functions much like a subway system in other cities except that many of the trains travel above ground, or are elevated. You pass by office building, shops, and apartments, essentially on the 2nd floor level where you can look into the buildings. Fun for the passengers, probably not so much for those inside. Choose from the various lines - Blue, Brown, Green, Orange, Red, Purple, Pink, and Yellow. Explore the L Train Maps and plan a ride. We have traveled on them several times and they are convenient and cheap. Most tourists take the Loop (downtown region) just to experience the train system. Fares are $2.25.

6. See Navy Pier. Although a bit touristy in spots, Navy Pier is a classic landmark for Chicago. It sits out near the water away from the skyscrapers so the views looking back towards the city are amazing. If you have kids, this is a must as there are rides, restaurants, and lots of small shops. At night you can watch fireworks during the summer months. We took the water taxi from downtown out to Navy Pier and were there as the sunset in late September. Beautiful to watch the sun go down between the buildings in the distance. Another popular event on Saturday nights are the all the harbor dinner cruises that depart from Navy Pier. Get dinner while you set out on the water. Check out the website - Navypier.com - get information on dinner cruises, rides, firework showtimes, or learn about the Children's Museum.

7. Experience the Magnificent Mile. Perhaps the most famous street in Chicago is Michigan Avenue. Just north of the Chicago River is the area known as the Magnificent Mile. The restaurants, stores, hotels, and buildings will keep you busy for hours. Shopping is a big business in any city, but the stores found on the Magnificent Mile like Tiffany & Co., Saks Fifth Avenue, Niketown, and Cartier are all worth a look. The American Girl Place is popular spot for parents with little girls and the Lego shop has always been a favorite of my sons. Stop into the John Hancock Center to take a ride to the observatory level and get some great views of the city.


8. Dining/Restaurants. One of the highlights of a recent trip to Chicago was going to Girl and the Goat Restaurant. If you are not aware of the show Top Chef, Stephanie Izard was a chef on that show a few years back and she started this restaurant. We waited for almost 90 minutes just to sit down on a Saturday night, but the food was amazing. The atmosphere was just right as we were able to sit back near the kitchen and watch the food being prepared. If you are a true foodie, then going to Grant Achatz Alinea (http://www.alinea-restaurant.com/) will be a highlight of your trip. I went there with my wife and it truly is an amazing meal with 18 courses ($210 - not including drinks). Go with an appetite and an open mind as the food is served in a rather artsy format. Other smaller places to try out are the Purple Pig (www.thepurplepigchicago.com) and C House which is attached to the Affinia Hotel on Superior Street. For a real basic breakfast or lunch, we highly recommend a spot at the base of the John Hancock Center called L'Appetito. Perfectly made to order sandwiches, soups, and a huge selection of morning pastries, muffins, etc. The staff is friendly and the food was delicious. See their website at http://www.lappetito.com/.

9. Wrigley Field - See Game or Take Tour. I would put this one at a much higher spot than #9, but not everyone feels the same about sports. The fact is that Wrigley Field is the 2nd oldest ballpark in baseball (built in 1914) and the history and nostalgia are worth the visit even if you aren't a baseball fan. The Chicago Cubs call it home, but the Bears and even the Blackhawks have played here. A game would be the best option to experience Wrigley at its finest, but I've done the tours and they are well worth the $25. The tours take you to places within the ballpark that most visitors don't get to see otherwise. See our Review of Wrigley Field Tour Here.

10. Chicago Museums. Let's be honest, the weather in Chicago doesn't always have the sun shining, so getting indoors during the rain or snow makes a lot of sense. Museums are a great way to learn about the city and get some art appreciation into your vacation. The two most famous museums are the Art Institute of Chicago and the Museum of Contemporary Art. If you had time to only see one, go with the Art Institute of Chicago. Admission is under $20 for an adult. When you enter the museum get a brochure with the floor plan and take a look at the back where they give you schedule if you only have about an "hour" to see things. Nice collection of Impressionism on the 2nd floor and some Dali and Picasso on the 3rd floor. The first floor has more ancient art and artifacts from the Romans, Greeks, Chinese, and Japanese. The Contemporary Art Museum was worth the visit, although you can get through most of it within 1 hour. Nice cafe - Puck's at the MCA - Wolfgang Puck that is.

11. Blues Music. The music scene in Chicago is thriving and the "Blues" are still a big draw at many a venue. The top spots for blues music are Kingstonmines.com, Buddy Guy's Legends, and B.L.U.E.S.. Most require some kind of cover charge or a drink minimum in order to sit down and listen.

12. Shopping. Not necessarily my favorite thing to do while visiting a city, but from the amount of people I witnessed on the Magnificent Mile in Chicago, it's clear that many tourists flock to the retail stores. Some popular spots include:
  • Tiffany & Co. - E. Superior St. and Michigan Ave.
  • Saks Fifth Avenue - located on Michigan Ave. just south of E. Superior St.
  • Cartier Chicago - north of Ontario St. on Magnificent Mile
  • Gap - East Ohio St. and Michigan Ave.
  • American Girl Place - if you have a daughter this is a must stop - E. Pearson St. and Michigan Ave.
  • Niketown - North of E. Erie St. on the mile
  • Souvenir Shops - everywhere you look - go with a Bears or Cubs shirt or jersey
  • Sephora - E. Grand Ave. and Michigan Ave.
  • Burberry Chicago - across Cartiter (see above)
  • H&M - just south of E. Chesnut St. on the Magnificent Mile
  • Lego Store - perfect location next to American Girl Place