Chicago Destination Guide
Have you BEAN to Chicago? There is an endless list of things to do (and eat) in Chicago, so we are here to help you prioritize your options! First, Chicago is a foodies dream come true, be sure to pack your appetite! It is also a very lively city. It is filled with culture, arts, outdoor activities, and many tourist attractions. We filled our visit with eating, drinking, biking, and amazing Chicago memories. Our recommendation is to visit Chicago in the summer, there truly is nothing better. No matter when you visit, you will leave know you want to return to the windy city one day soon.
Check out our list of places to see and food/drinks to try. We explored Chicago for three days and covered a lot of ground!
Places to See
Millennium Park – It is hard to imagine Chicago without it’s amazing public park, but this space was converted in 2004 from an industrial wasteland to an awe-inspiring, creative, green space for Chicagoans and tourists alike.
Cloud Gate “The Bean” – A signature landmark in Chicago located in Millennium Park. The bean is great for selfies, signature pose photos, and creative shots of the Chicago architecture.
Crown Fountain – Crown Fountain combines a great location to cool off from the summer heat and a unique art display. The fountain is comprised of two towers and a reflecting pool. The towers project video images of 1,000 Chicagoans to represent the diverse demographics of the city.
Buckingham Fountain – Buckingham Fountain is close to Millennium Park, but it is actually located in Grant Park. It is one of the largest fountains in the world and operates from April to October (another reason to visit Chicago in the summer!) The fountain is an excellent spot for photos with Lake Michigan or the Chicago skyline in the background.
Art Institute of Chicago – If your plan was to visit the Art Institute to recreate memorable scenes from Ferris Bueller’s Day Off, it will cost you $25 per person in admission. Most of the museums in Chicago are pricey, but if you are interested in art or are looking to fill a rainy day this is a great option.
Chicago Theater – The marquee outside of the theater is an unofficial emblem of the city. This historic building is located in the loop area of Chicago and is easy to access for a photo (selfies are highly recommended!).
Magnificent Mile – The ‘Mag Mile’ is any shoppers dream come true. The street is home to many mid-range to high-ends stores including my childhood favorite, the original American Girl Store. There are many restaurants and hotels located along this street, including the John Hancock Center.
Navy Pier – There is always something happening at the Navy Pier, but the pier’s most famous attraction is the Ferris Wheel. The Navy Pier is geared towards families and tourists. It is worth a quick visit, but be aware that the restaurants are priced much higher here than in other parts of the city. If you only have limited time in Chicago, I wouldn’t put Navy Pier on the top of your must see list.
Lincoln Park Zoo – A free zoo in the city! Chris is one of those people that thinks zoos are depressing, which can be a valid point. Our zoo experience was actually very positive, especially since we were visiting in June and were able to see many baby animals!
North Avenue Beach – There are many popular lakeside beaches to visit, but if you can only go to one then go to North Avenue Beach. It has breathtaking views of the city from the beach. North Avenue Beach is on our Top 7 Places to take the BEST Instagram Photos in Chicago check out the other places using the link.
The 606 – The 606 is an elevated trail for bikers, runners, and walkers and it is A-MAZING. As soon as you reach the trail you are surrounded by greenery and art that you forget you are in a city. The trail has a cushioned area for runners and plenty of room for the bikers. There are water fountains, bike repair stations, and benches along the trail. If you love biking or running, then you need to check out this trail during your visit to Chicago. You won’t regret it, you will probably feel like you want to move here to be able to use the trail everyday!
Wrigley Field – Historic Wrigley Field is home to the Chicago Cubs and located in the heart of northern Chicago. It is the second oldest baseball park in the US (after Fenway) and it is worth a visit even if the Cubbies aren’t in town. We were lucky enough to catch a Cubs game and watch them beat their rivals the St. Louis Cardinals. Check out the bars in Wrigleyville after the game! Go Cubs Go!
The Second City – The Second City Comedy Club is a Chicago staple. It has been around since 1959 and is known for being the world’s premier comedy club. It has a notable list of alumni including Tina Fey, Steve Carell, and Bill Murray. We went to a late night show called, “The Winner of Our Discontent”. When purchasing your tickets there are a few different seat options Premium, General Admission, and Restricted View. The theater didn’t seem to have a bad seat in the house, so I wouldn’t worry about purchasing the premium tickets, just arrive early and you should get a great seat!
What to Eat/Drink and Where to Find It
Chicago Style Deep Dish Pizza – Deep dish pizza should be on the top of everyone’s list when visiting Chicago. Be sure to order the pizza Chicago-style and don’t order too much. Your eyes will be bigger than your stomach, the deep dish pie is deceivingly filling! Also, don’t worry it is totally acceptable to eat deep dish pizza multiple times on your trip to Chicago. We had to try the pizza at both Lou Malnati’s and Pizano’s! Check out our blog post on Chicago’s Famous Deep Dish Pizza!
Chicago Hot Dog – Looking to try all of the famous Chicago grub? Then you need to try a Chicago Dog. We grabbed one at Portillo’s, a chain restaurant specializing in Chicago food. A traditional Chicago dog has a ton of toppings: mustard, relish, celery salt, chopped onions, sliced tomato, a pickle, and sport peppers all on top of a hot dog and stuffed into a poppy seed roll. The best part is that it costs under $3!
Garrett Popcorn Shop – Garrett’s Mix (Chicago Mix) – One of my favorite things to eat in Chicago is Garrett Popcorn Shop. Warning: you will become addicted to this popcorn! I always choose the Garrett’s Mix or Chicago Mix as I used to call it. This is a bag of popcorn with cheddar popcorn and caramel popcorn mixed together. It is messy, but it is oh so delicious.
Stan’s Donuts – A popular Chicago cafe that is found throughout the city. Stop in for an instagram-able donut and it will taste as good as it looks!
John Hancock Signature Lounge – A great drinking location is at the John Hancock Signature Lounge located on the 96th floor of the John Hancock Center. The drinks are pricey, but the views are priceless. Travel Tip -> Plan to get to the lounge about 30 mins before sunset and experience the view transition from day to night. Don’t be discouraged if you end up with a table that has an obstructed view. The staff is really good about moving you closer as others leave. One of the good features about the drinks being overpriced is that many people do not stay long!
Breweries: There are countless breweries in Chicago, so many that we spent a day brewery hopping. You can learn more about the breweries that we visited on our Drunken Traveler page – The Chicago Brewery Tour. In this article we will highlight – Revolution Brewing, Dryhopped Brewing, and Hopewell Brewing.
If we had one more day in Chicago, we would have visited…
Humboldt Park and had a drink at the Green Mill Cocktail Lounge
Check out our other city Destination Guides around the USA – featuring Austin, San Antonio, and Santa Fe!
