11 must-do activities when visiting Chicago
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.
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.
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.
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
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
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| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
| 2X | Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.
Rewards Rate
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 3X | Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com. |
| 2X | Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com. |
| 1X | Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases. |
Intro Offer
You may be eligible for as high as 100,000 Membership Rewards® Points after spending $6,000 in eligible purchases on your new Card in your first 6 months of Membership. Welcome offers vary and you may not be eligible for an offer.As High As 100,000 points. Find Out Your Offer.Annual Fee
$325Recommended Credit
Credit ranges are a variation of FICO® Score 8, one of many types of credit scores lenders may use when considering your credit card application.Excellent to Good
Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.