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11 must-do activities when visiting Chicago

Aug. 28, 2021
7 min read
Chicago's Lakefront on Lake Michigan
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Chicago is a gem in the midwest with so much to offer. Yes, this city offers great food (you don’t want to miss the classic deep dish pizza), but there’s so much more to explore.

Chicago has something for everyone — a great mix of nature, art and culture. With two airports — both accessible by public transportation and serviced by all major airlines — flight options abound. There's no shortage of points hotels either.

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Here's a list of 11 must-dos when visiting the Windy City.

Dive into a deep-dish pizza

When you first arrive, deep-dish pizza is likely top of mind, and rightfully so. You’ll find great deep-dish pizza offered at the famous Lou Malnati’s Pizzeria. If you’re looking for hidden gems, check out Art of Pizza or Pequod's. Be prepared for a serious food coma afterward as these pies are no joke.

Walk along the Chicago riverwalk

The riverwalk is a centrally located, 1.25-mile walking path along the Chicago River. The riverwalk was built in phases over the past decade with murals, statues and other art pieces along the way. You’ll find tons of great restaurants and bars with outdoor dining right on the riverside. If you’re walking by the river in March around St. Patrick's Day you’ll also catch the river when it's dyed bright green.

The Chicago River for the St. Patrick's Day Parade. (Photo by Yannick Tylle/Getty Images)

Related: Use Points at These 9 Family-Friendly Chicago Hotels

Explore the lakeside trail on Lake Michigan

Lake Michigan is one of the world's largest lakes with 18 miles of lakeside trail running along the city’s eastern edge. This paved trail is perfect for walking, biking and even access to swimming. Check out Montrose Beach, Oak Street Beach, or North Ave Beach right along the route. You can rent bikes at multiple points along the trail or even get a guided Segway tour through the South Loop section of the trail. The lakeside trail connects directly to the Riverwalk and multiple downtown access points for easy access to your favorite hotels.

Explore Chicago’s waterways

Getting out on the river or lake is even better than walking alongside it. You can rent kayaks and paddle boards if you’re the adventure type or enjoy the experience from a larger boat. You can rent boats by the hour in the summertime or book a tour. A variety of providers offer architecture tours which are a perfect way to get to know the city’s history while enjoying your time on the river. If you love to kayak and also want the history, don’t miss out on the architectural kayaking tours.

Related: American Airlines unveils sweeping Chicago-focused route expansion

Visit the Art Institute of Chicago

Speaking of history and culture, this well-known museum in Chicago is one you don’t want to miss. The Art Institute of Chicago is located right next to the famous Cloud Gate sculpture in Millennium Park also known as “The Bean”. This museum is one of the nation's oldest and largest art museums, with close to 300,000 pieces in its collection. This indoor and outdoor museum also has rotating special exhibits like the Obama portraits that keep even the most frequent visitors coming back.

Chicago August 2014. (Photo by Clint Henderson/The Points Guy)

Take a walk in the parks

If you’re looking to save a little during your trip, Chicago has a lot to offer that doesn’t cost anything at all. There are 570 parks located in the Chicago area and while the weather is nice, you never know what fair or festival you might stumble upon while you’re exploring. Lincoln Park, Grant Park, Millennium Park, and Garfield Park are among the most famous. The 606 is a newer addition to the city, finished in 2015. This formerly abandoned stretch of elevated railway track is now a 2.7-mile pathway that connects several parks and public art installations.

Related: Layover lowdown: Chicago O’Hare International Airport

Enjoy a local farmers' market

Chicago is known for great food and heading to the farmers' market can help you take full advantage of all the local land has to offer. There is a farmers' market happening almost every day of the week during the summertime. The Logan Square, Lincoln Park, and Green City farmers' markets are the most well-known weekend markets. They each offer a variety of local fresh fruits, vegetables, meats, and artisan craft products. If you’re looking for an indoor option open during the week, the Chicago French Market, located in River North, stays open year-round.

Visit the Maxwell Street Market

If you’re looking for a bargain, head to the historic Maxwell Street Market located near the West Loop. The Maxwell Street Market is a yearly tradition in Chicago, featuring a variety of handmade crafts, food and live music. The market first opened in 1912 and has become a melting pot of cultures within the Chicago community. Currently, you’ll find the market open, weather permitting, from 9 am - 3 pm on the 1st and 3rd Sundays of the month between June and December.

Related: Chicago O’Hare vs. Midway: Which Airport Should I Fly Into?

Check out a Cubs game

Chicago is known for its sports teams and if you’re visiting during baseball season you should plan to catch a game at Wrigley Field. Heading out to a ball game is such a quintessential Chicago experience. Before you head inside, take a second to look at the statues of former Chicago Cubs stars located on the corner of Addison and Clark streets. If you’re traveling with a younger fan watching a game for the first time, head to the fan services desk for a first-time attendance certificate. Make sure you’re there between the National Anthem and the first pitch to secure your certificate!

Spend the evening in a speakeasy

In a city with such rich history, it’s not surprising that Chicago also has several bucket-list-worthy speakeasies. Although the entrances may no longer be impossible to find, you are still getting a more unique taste of what Chicago has to offer. There are quite a few well-known options like Violet Hour and the Chicago Music Lounge, highly regarded for good reason. However, inside the Green Door Tavern, you’ll find The Drifter, a speakeasy known for the historic vibe that comes from its history as an actual speakeasy during the prohibition era.

Attend one of the city’s music festivals

Lollapalooza is one of the biggest music festivals in the country. (Image courtesy of Maclay Heriot/Lollapalooza 2016.)

Chicago is known for great live music and an incredible concert scene. You may have heard of Lollapalooza, the Windy City Smokeout, or the Pitchfork Music Festival. These large music festivals are just a few of the yearly staples that offer something for every musical taste. Chicago is also home to smaller downtown music festivals that showcase blues, jazz, gospel and house. There are also tons of music festivals that happen throughout Chicago neighborhoods like Wicker Park East.

Related: 7 Things to Do in Chicago With Kids

Related: Guide to Planning a Family Trip to Chicago

Photo by photoiva / Shutterstock.com

Featured image by (Photo by photoiva / Shutterstock.com)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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