America’s coasts tend to steal the limelight from the rest of the country, with travelers setting their sights on New York and Los Angeles. But those cities can be pricey. And perhaps you’re looking for a trip not featured on every third Instagram account.
For me, Chicago checks all the boxes. Nestled against Lake Michigan, Chicago feels like a coastal city even if that isn’t technically true. Plus, you could visit every weekend for a year and not run out of things to do. Here are the must-sees and must-dos for your first visit to Chicago and beyond.
Best Times to Go to Chicago
The best time to visit Chicago is in the summer, as that is when most of the city’s biggest events happen. That includes the Chicago Air and Water Show (Aug 19-20, 2023), the Taste of Chicago (Sept 8-10, 2023; see below), and the Lollapalooza music festival (Aug 3-6, 2023; Lollapalooza.com). Visiting in summer means you’ll also be able to spend time at Chicago’s numerous beaches and catch a Cubs game at Wrigley Field or the White Sox at Guaranteed Rate Field.
Another great time to visit Chicago is in the winter. If you don’t often see snow, downtown Chicago will be especially beautiful at this time. You can shop at the Christkindlmarket or go ice skating in Millennium Park. And the Chicago Auto Show takes place every February.
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Bad Times to Go to Chicago
There are no bad times to visit Chicago, but the city isn’t as lively during the cold-weather months outside the holiday season. And when the weather is cold, but not quite cold enough for snow and ice, the city will be even less appealing because ice skating may not be an option.
Generally, January and February can be relatively uneventful in Chicago, especially if the Chicago Auto Show doesn’t interest you. If that is the case, you’re better off visiting either during the holiday season or when the weather is a little warmer.
Average Cost of a Chicago Vacation
The average cost of a Chicago vacation can vary significantly depending on the length of your stay and your accommodations. But suppose you plan to stay for one week in a nice hotel and fully immerse yourself in the culture during your trip. In this case, you can expect to spend about $1,260 for a single person and about $1,684 for a couple. It can be more expensive when traveling with a family.
Remember that these are only estimates, and you may be able to stay in Chicago for less. For example, a single person traveling on a budget could take a one-week vacation to Chicago for less than $1,000. Again, it depends on where you stay and how much you spend at local attractions, bars, and restaurants.
10 Fun Must-Dos in Chicago
Chicago is known for its music scene, great food, and world-class museums, among other things. There is so much to do in Chicago that choosing just 10 attractions isn’t easy. My picks let you experience the city for what it really is — gritty but determined and altogether incredible.
If you plan to do everything on this list, consider purchasing a Chicago CityPASS (CityPass.com/chicago). While these passes aren’t cheap ($134 adults; $104 children), they include entry to several of Chicago’s most popular attractions and will save you money overall. Also consider buying a weekly or monthly pass for CTA, Chicago’s mass transit system. Renting a car is another option, although it isn’t always the cheapest.
As far as where to stay, you can’t go wrong with areas like West Loop, South Loop, and River North. Or if you want to live more like a local, consider neighborhoods like Lake View, Logan Square, and Old Town. Of course, hotels can be expensive, so you’ll want to save money on accommodations whenever possible. From these areas, you can access most of the spots on this list via the CTA system.
1. Millennium Park
Have you even visited Chicago if you don’t see Millennium Park? The park features iconic art installations such as Cloud Gate (known colloquially as “The Bean”) and the Frank Gehry-designed Jay Pritzker Pavilion, an amphitheater that hosts live music. There’s also Crown Fountain, incorporating a water fountain and oversized LED screen projecting images of faces. Other highlights include Maggie Daley Park, where you’ll find an ice skating ribbon and an outdoor rock-climbing wall. 201 E. Randolph St.
2. Willis Tower Skydeck
Formerly the tallest building in the world, Willis Tower stands 1,451 feet tall. Naturally, the Willis Tower Skydeck is the best way to view the city. Chances are, you’ve already seen photos of people visiting the Skydeck, with its clear-glass area simply called The Ledge. Adults $41, youth $33. TheSkydeck.com
3. Original Rainbow Cone
If you find yourself in Chicago during the searing summer months, you’ll need a way to cool down. Fortunately, Chicago has plenty of ways to do that, and one of the best is to visit the original Rainbow Cone in the Beverly neighborhood. The ice cream shop has been around for over 95 years and is famous for its original flavors: orange sherbet, pistachio, Palmer House, chocolate, and strawberry. 9233 S. Western Ave. RainbowCone.com
4. Art Institute of Chicago
Founded in 1879, the Art Institute is one of the oldest and largest art museums in the world. Featuring countless masterpieces, it has one of the best collections of Post-Impressionist paintings outside France. Look for classics like “A Sunday Afternoon on the Island of La Grande Jatte” and Picasso’s “The Old Guitarist.” The Art Institute’s permanent collection features nearly 300,000 works of art. 111 S. Michigan Ave. Adults $32, seniors and students $26, children under 14 free. Artic.edu
5. Taste of Chicago
Chicagoans know that Taste of Chicago is a unique opportunity to try the city’s many flavors all in one place. Sure, the food tends to be overpriced, but there’s no other way to experience so many Chicago dishes in so little time. (And the cost of food is a great excuse to earn credit card rewards.) Years ago, I saw a Counting Crows concert at the Taste, which is completely free to attend. Of course, events vary each year, but it’s worth the investment if you’ll be in town while the Taste is happening. Sept 8-10, 2023, in Grant Park.
6. Celebrate the Irish Spirit
People from all over the world have made Chicago their home since the start of the Industrial Revolution, but the Irish are some of Chicago’s loudest and proudest. As a result, Chicago is home to countless Irish festivals and parades. The St. Patrick’s Day parade downtown (ChicagoStPatricksdayparade.org) and the South Side Irish Parade (SouthSideIrishParade.org), also in March, are two of the best ways to experience Chicago’s Irish culture. And if you’re in Chicago for the downtown parade, be sure to check out the dyeing of the Chicago River. 2024 dates TBD.
7. Museum of Science and Industry
If you nerd out over science stuff, you can’t miss the Museum of Science and Industry (MSI). Touted as the largest science center in the western hemisphere, MSI was founded in 1893. Its marquee exhibits include the German U-505 submarine captured during World War II (admission is $18 for adults on top of museum entry fee), a full-size replica coal mine, and the command module from Apollo 8. If you buy a membership to the museum ($95 per year for individuals), you get unlimited entry at no extra cost. 5700 S. DuSable Lake Shore Dr. Adults $25.95, children 3-11 $14.95. MSIChicago.org/
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8. Shedd Aquarium
The Shedd Aquarium opened in 1930, and for a time its 5 million-gallon capacity was the largest in the world. It is home to 32,000 animals today, including fish, marine mammals, birds, snakes, amphibians, and insects. Some of its most popular species are penguins, sharks, sea otters, and turtles. The CityPASS program includes unlimited entries to the Shedd. 1200 S. DuSable Lake Shore Drive. Adults $40, children $30. SheddAquarium.org
9. Vito & Nick’s Pizza
If you think Chicago is all about deep-dish pizza, think again. I grew up just blocks from Vito & Nick’s, which has been featured in countless articles and TV shows over the years. Despite being a hole in the wall, the pizzeria draws people far and wide for arguably the best thin-crust pizza in Chicago. Located in Chicago’s Scottsdale neighborhood (or Ashburn, depending on who you ask), Vito & Nick’s is an escape from downtown, but it’s worth the trip. 8433 S. Pulaski Rd. VitoandNicks.com
10. Schubas Tavern
Located in the heart of the Lake View neighborhood, Schubas Tavern is housed in an old Schlitz brewery. The venue has a wide selection of drinks and food, and features an even wider range of live music, from indie to jazz. Perhaps the best part about seeing a show here is the intimate setting, which gives you an up-close-and-personal look at some great artists. 3159 N. Southport Ave. LH-St.com
Chicago is a one-of-a-kind city with some of the best food, entertainment, and architecture in the world. Although it can sometimes be overshadowed by cities like London and New York, you can have an equally good time in Chicago — and likely for less money. If you’re looking for fun for the whole family, you are sure to find it here.
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What are the most popular things to do in Chicago with kids?
The most popular things to do in Chicago include trips to Millennium Park, the Shedd Aquarium, and the Skydeck at the Willis Tower.
What are the best outdoor activities in Chicago?
The best outdoor activities in Chicago include visiting Millennium Park, Navy Pier, and North Avenue Beach.
What are 5 things that Chicago is known for?
It’s tough to narrow it down to five, but we’ll go with the Magnificent Mile, Second City, Millennium Park, Chicago Riverwalk, and Skydeck Chicago.
Photo credit: iStock/tunart
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