Chicago is one of the most vibrant cities in the world – combining an eclectic mix of sports, architecture, music, food and art. Located on the shores of Lake Michigan, the towering skyscrapers stand proudly over the beaches of Lake Shore Drive and the outdoor spaces of Millennium Park. Whether you want to enjoy a hot dog in the outfield at a Cubs game or visit the world-renowned Art Institute of Chicago, this city provides unlimited activities for even the most discerning travelers. You could never see all of Chicago in a single day but this itinerary will take you to its top destinations.
GUEST POST BY DEBORAH JANOWSKI
BLOG: Relaxed Nomad
What’s the best time to visit Chicago?
Chicago is known as the windy city and winter means it can be very, very cold, so the best time to visit Chicago is during the summer when the weather is a beautiful eighty degrees and sunny – and the outdoor parks and streets are alive with activity.
What’s good to know about Chicago?
Chicago is very compact, so the majority of sights are located in the downtown area which makes it easy to see a lot in a short period. North of Wacker Drive is where you can find most of the stores and restaurants of Michigan Avenue and south of Wacker Drive is Millennium Park, the Art Institute of Chicago and Soldier Field.
One Day in Chicago Itinerary
Follow this guide and make the most of your trip even if you’re short on time. These are the top sights and things to do during your one day in Chicago.
Millennium Park, Art Institute of Chicago
Begin your morning by walking Millennium Park. This park is home to the Buckingham Fountain, the Cloud Gate sculpture (often referred to as The Bean), large outdoor modern sculptures and gardens.
After touring the park, the Art Institute of Chicago is located at the southern end. The museum houses some of the most famous works of art in the world including Grant Wood’s American Gothic and Edward Hopper’s Nighthawks. After perusing the art, the Gage across the street is a local favorite for lunch complete with Scottish Eggs and Poutine Fries.
If you like sports, you may want to try to head a bit north to visit the historic Wrigley Field and catch a Cubs game on a beautiful afternoon. The stadium is home to a number of Chicago staples including craft sausages, hot dogs and buffalo chicken fries. And Chicago fans are typically very welcoming and happy to talk with visitors about their love of the city and their home teams.
Architectural Boat Tour
Or, if you don’t particularly like baseball or there is not a game in town the day you are visiting, you can go on one of the many architectural boat tours in the harbor of Lake Michigan to learn about the history and sights of the Chicago skyline from the water while enjoying a cool summer breeze.
Hancock Tower, Michigan Avenue
Many visitors will visit the Skydeck where you can purchase tickets to stand in a glass outcropping to see the entire Chicago area from the top of the Sears Tower. However, locals prefer to visit the Hancock Tower and the Signature Lounge on the 96th floor. As the sun begins to set, you can enjoy a glass of wine while enjoying a 180-degree view from your own table. Before or after visiting the tower, there is also time to stroll along the famed Michigan Avenue, which is always crowded with visitors from around the world and a large number of boutiques and stores.
Like any major city, there are simply too many places to eat in Chicago to pick just one. If you want to enjoy a Chicago pizza, you can stop at any of the pizza locations in the Michigan Avenue area. We won’t recommend one over the other (Lou Malnati’s, Pizzeria Uno, Bartoli’s, etc.) as that would simply lead to an argument with most Chicagoans over which is the best.
If you want something unique, you can enjoy dinner at the RL Restaurant right around the corner from the Hancock Tower. The RL Restaurant is attached to Ralph Lauren’s signature store and specializes in burgers and corned beef.
If you want something more lively, you can head over to Gibson’s on Rush Street by cab and either sit around the piano singing songs with the locals or head upstairs for a steak dinner.
After dinner, no trip would be complete without enjoying live Chicago blues music. This can entail a trip south to Buddy Guy’s Legends by Millennium Park. Or north to Kingston Mines in Lincoln Park. But whichever way you travel, cabs are plentiful and rides are short.
Where to stay in Chicago?
Aloft Chicago City Center
515 North Clark Street, River North, Chicago
The Aloft Chicago City Center is a modern boutique hotel located in the heart of downtown Chicago’s in trendy River North neighborhood. It features a modern fitness center and business center, as well as the lounge with a pool table. It’s walking distance to Millennium Park and many other popular sights.
20 West Kinzie Street, River North, Chicago
Kinzie Hotel is an upscale boutique hotel located in Chicago’s River North district, only a short walk to the famous Magnificent Mile. The hotel features fully designed, bright and modern rooms for a perfectly comfortable stay for all types of travelers.
Chicago Getaway Hostel and HI Chicago Hostel are two of the best hostels in the city, perfect for young travelers who want to socialize with others and meet fellow travelers. You can still be close to the city center and all the great sights without spending a fortune on the accommodation.
DAY TRIPS FROM CHICAGO
Day trips from Chicago are always a great idea if you have the time. This big city certainly offers a lot, but heading out of town certainly has its advantages, too. There is plenty to see, and you can even visit another US city rather painlessly. The options are numerous, and here’s what you’ll want to check out.
A day trip from Chicago to Milwaukee is a great solution for tourists who want to experience as many US cities as quickly as possible. It will only take you about an hour an a half to get there, be it by car or by train. There are loads of very interesting museums to see (Harley Davidson Museum first comes to mind), great food to enjoy and delightful people to meet. You certainly won’t regret visiting this lively city.
A short ride west from Chicago (about 30 minutes) is Oak Park. Now, this quaint little town for those who want to enjoy arts and especially architecture. The famous architect Frank Lloyd Wright was so prolific here that he has his own district, but there are also many other types of art worthy of checking out in this quaint little town. This is a vibrant, diverse and chilled out community and a perfect place to spend your day.
Indiana Dunes National Lakeshore
If you want to enjoy some beautiful nature, head to Indiana Dunes National Lakeshore. Yes, you will have to cross the state line, but it’s only about an hour’s drive away from Chicago. This is an excellent place for bird watching, as there are literally hundreds of different kinds of birds that migrate through here. Swimming, hiking and fishing are also some of the things you can do, so if you want an active outdoors vacation, this part of Lake Michigan is definitely for you.
Last, but most certainly not the least, you can head on a day trip from Chicago to Holland. As you can see from its name, this little town is very proud of its Dutch heritage. And it shows! This place is home to the Tulip Time Festival, and you can see these beautiful flowers wherever you look. Not only that, but you can also enjoy some excellent Dutch cuisine and absolutely beautiful houses and cobblestone streets. This really is an escape into a dreamworld!
Extra tips for visiting Chicago
– We recommend against using a rental car. Parking in Chicago is difficult and taxis are everywhere and very convenient, so it is quite easy to walk and catch a quick ride anywhere in the city.
– Traffic to and from the airports in Chicago can be very congested, so plan your trips accordingly.
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Make sure you have everything you need
What to pack for your next trip?
Make your next trip as simple and as enjoyable as possible by packing smart. It’s amazing how much stress top travel items can save you, so choose carefully.
Things like lightweight travel backpacks, for example, are ideal for short trips and allow you to move around with ease, and a passport holder will make sure you keep your documents safe at all times.
Check our travel checklist guide for 2021 to make sure you haven’t missed anything, and travel to your next destination in style and with maximum comfort.
Deborah runs the travel website, RelaxedNomad, which specializes in sharing itineraries, notes and travel plans for entire areas of the country and road trips. One of her goals is to make traveling easier for families while finding truly unique activities in unusual places.