For some travelers, Chicago may always live in New York’s shadow. Heck, it is called the Second City, after all.

But make no doubt about it, when visiting Chicago, you’ll quickly discover this is a city that stands on its own. Nestled up against Lake Michigan, the midwestern city of Chicago is known for a lot of things, from deep-dish pizza to deeper snow drifts. From jazz and comedy to Polish sausages and Italian gangsters, Chi-Town isn’t lacking for hometown traditions.

But when actually visiting Chicago, you’ll discover that the Windy City runs deeper than these popular sounds, sights and tastes. It’s a multi-cultural melting pot overflowing with passionate sports fans, international commerce and parades-a-plenty. So book your tix for a night of Live Jazz at Buddy Guy’s Legends and take in some laughs in the city that groomed the likes of John Belushi, Bill Murray and Tina Fey. There’s another reason the Second City gets its name — visiting Chicago for the first time means you’ll soon be planning your next trip.

When to Visit Chicago

Similar to New York, Chicago’s harsh winters mean that springtime — specifically, April through May — is prime time for tourism. It’s when travelers converge for events including the Chicago Comic & Entertainment Expo and Mayfest. Consequently, flights and hotels are more expensive, and tix and reservations are harder to snag.

That said, if you can brave chilling winds and temperatures that often dip below freezing, there is fun and value to have in December, when other travelers head for warmer shores.¹ It’s a great time to catch a Red Wings game — Chicago is a hockey town — head out to one of the city’s many public skating rinks, and visit the Christkindlmarket, a throwback, open-air holiday market experience exported from Nuremberg, Germany from November through December.²

Right-Sizing Your Trip to Chicago

Measuring up at an impressive 234 sq. miles, Chicago is bigger than Boston, Paris and Milwaukee — combined. While it’s a bit easier to navigate than New York and LA, it’s also not wise to attempt to visit Chicago — all of Chicago —in a single weekend.

We’ve taken the time to break down Chicago by its major geographic areas, noting some background and suggesting some attractions and activities for each:

Visiting Central Chicago

When tourists and first-time travelers think of Chicago, they often conjure up an image of sky-high towering, urban parks and thriving street parties. Welcome to Central Chicago, the city’s commercial hub. This area is highlighted by The Loop, which sets the pulse of downtown Chi-Town and is home to world-famous edifices including buildings designed by Louis Henri Sullivan and Ludwig Mies van der Rohe.

One of the area’s hubs of art, culture and entertainment is sprawling Millennium Park. The mixed-used space is home to avant-garde architecture, art installations and landscaping. Highlights include Cloud Gate, the enigmatic, 110-ton bean-shaped sculpture. Millennium Park is an ideal backdrop for a morning stroll, a live concert and your very first Segway ride. Best of all, park and exhibit entry is free!³

If you do plan on visiting Chicago over the holidays — in mid-November, specifically — and you love a parade, then we’ve got one for you. The Magnificent Mile, a popular commercial and shopping district, plays host to the annual parade that takes the same name: the Magnificent Mile Lights Parade. Join Disney characters and get ready to “ohhh” and “ahhh” at more than one million lights strung across 200-plus trees as well as fireworks that are set off over the Chicago River.

In case you didn’t already know, parades and street parties are a big deal throughout Chicago, from the Chicago Pride Festival and Puerto Rican Parade occurring at the end of June to parades held in conjunction with holidays, including the St. Patrick’s Day Parade and New Year Parade, a Chinatown—South Side spectacle celebrating the Lunar New Year.⁴

Visiting Chicago’s North Side

Don’t be fooled by Chicago’s harsh winter. Summers are still in play. And nowhere is this on display more than the North Side, where Lake Michigan’s beaches hug the tip of the city. Cap off a day of sunning on the beach with an evening of winning at historic Wrigley Field with the hometown Cubs. And if it’s an off-day, tour the century-plus-old park and take a sure-to-be-shared selfie in front the field’s famed ivy wall. If it’s game day, join the crowds pregaming at Wrigleyville — a section of the Lakeview neighborhood encompassing the stadium — to learn what it’s truly like to be a passionate Cubbies fan. (Pro tip: It’s OK to mention “The Curse of the Billy Goat” again since the Cubs won the World Series in 2016.)⁵

You can’t talk about the North Side without at least mentioning Navy Pier — so we will. While it’s a bit overcrowded for some, the Navy Pier brings together boat rides, the giant Centennial Wheel, sunset yoga, tours, public art exhibits and so much more.⁶ But if you want to take a hike away from the bustle and bustle, hop on the 606, an elevated urban pathway stretching nearly three miles through Bucktown, Logan Square and Humboldt Park (located in Chicago’s West Side). Whether you run, walk or bike, the 606 is built for self-guided tours of Chicago, including plenty of inviting green spaces, restaurants and watering holes along the way if you want to make a day of it.⁷

Finally, we should note that the North Side also offers a heterogeneous mix of residents, and consequently, a unique chance to immerse yourself in the food, drink and overall culture of Eastern European and Puerto Rican communities.

Visiting Chicago’s West Side

The West Side is the nexus of old and new, where venerable parks gather folks together beside neighborhoods undergoing gentrification. It’s home to the United Center, where the NBA’s Bulls and Blackhawks call home, as well as Garfield Park Conservatory, among the most well-known botanical gardens in the country.

Perhaps the conservatory is so popular because its attraction bridges the Great Outdoors and Indoors, creating a seamless visitor experience whether you’re looking to learn about growing or just admire the 10-plus acres of gardens. Be sure to stop by the Palm House, which mirrors a tropical landscape, the children’s garden if you’re traveling with curious kiddos, and Sensory Garden’s interactive labyrinth. The Garfield Park Conservatory shares one more thing with many of the destinations in this article: it’s free!⁸

Visiting Chicago’s South Side

Welcome to the largest area of Chicago by size: the South Side.

This former site of the city’s sprawling stockyards is home to the White Sox, Jackson Park (site of the 1893 World’s Fair) and perhaps the biggest, most historic parade of them all: the Bud Billiken Parade. This celebration of African-American culture and history equally focuses on the past and future, bringing together residents and tourists alike for 90-plus years. The event, held in early August, boasts marching bands, floats, dance teams, contests and more traveling a lively route down King Drive.⁹

The South Side also houses the Museum of Science and Industry, whose 400,000-plus sq. ft. feature a real WWII German submarine, a five-story movie screen, and a host of exhibits designed to pique the visitors’ curiosity toward science and engineering.¹⁰

Getting There & Getting Around

Bringing more than 80 million passengers a year to 260 destinations each year, O’Hare International Airport is a global aviation hub. This means more carriers, more choices, more airport meal options — and more crowds. Midway Airport, which is a bit more convenient to the city with just a 10-mile airport transfer, serves about 80 destinations, providing flyers with smaller crowds and fewer amenities. (Although a modernization program looks to change that.) In other words, you have a choice. Be sure to shop flights traveling through both airports to find the most convenient flights at the right price.¹¹

Once you’re here, the Chicago Transit Authority (CTA) has your ticket to ride, whether it’s by subway, elevated train or bus. Check out the CTA transit routes to see how to plan around your itinerary.¹² One note: if you go the daily pass route, know that it’s good for 24 hours from the time of purchase; so don’t go ditching your pass when the clock strikes midnight.¹³

Ride-sharing is also option. And Chicago offers more than the standard Lyft and Uber options. Try Via if you’re OK sharing a car with other riders, Jayride if you’re just chasing airport transfers and Blackbane for more luxurious options.¹⁴

Finally, if you’re ready to explore Chicago by foot, consider one of the city’s more walkable neighborhoods. These include the West Loop’s Fulton Market, home to Google’s local offices, interesting architecture and plenty of popular bars. Also, the Near North Side is especially known for its walkable neighborhoods, so when in doubt, look there.¹⁵

Where to Stay When Visiting Chicago

When you’re seeking the right landing place after a long day of exploring a new city, you may be seeking everything from comfort and convenience to value. But what about being cutting edge?

Welcome to the future.

At EMC2, located on the Magnificent Mile and also known as “the robot hotel,” you’ll bump into brainy art (think: an LED display of Albert Einstein) and in-room Amazon Echo Dots. The décor is uber modern and the features are user friendly. But what really sets the hotel apart is a pair of robot butlers, Leo and Cleo, which can fetch that toothbrush you forgot or other gotta-have items.^{16, 17}

There’s cutting edge, and then there’s value. And the Inn of Chicago tops many of the best value lists when it comes to Windy City lodging. Similar to New York’s hotel scene, the Inn of Chicago proves that your dollar can stretch farther at boutique hotels than chain lodgings. And this Central Chicago spot gets it done with the details, ranging from its collection of quintessential Chicago photography to its walkable location and rejuvenating pillow-top mattresses.

Also be sure to check out the Majestic Hotel, an in-demand Lakeview option featuring exquisite design, free fresh-baked cookies, mini-fridges and a fitness club complete with classes and a lap pool. For a summer weekend booked about two months in advance, we found rates for $225 a night.¹⁸

Maybe the most apt metaphor for visiting Chicago is that simmering, delicious deep-dish pizza. Just one trip — a single slice — can be filling. So enjoy Chicago by the slice, or even one link at a time. You can always come back for more. And you will.

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