Your kind of Chicago – five insider ways to experience the Windy City

Lakefront breezes, sandy beaches, striking architecture, acclaimed restaurants, theater, and world-class museums – Chicago has it all. And with our direct flights from Helsinki, diving into the city’s vibrant energy couldn’t be easier. 

1. Take a walk on the north side

If you’re staying downtown, ask your concierge or any bellman for the quickest route to the lakefront – it’s likely walkable from your hotel – and let the fun begin. From downtown, head north along the lakefront path, which runs the entire length of the city. Watch out for bikers, rollerbladers, and runners! It’s a popular route, with Lincoln Park to your left, Lake Michigan to your right, and the skyline at your back.

First, you’ll hit Oak Street Beach, where you’ll want to grab a bench and do some people-watching. Keep heading north until you get to the North Avenue Bridge, the only bridge spanning Chicago’s famous Lake Shore Drive.

Cross over, and you’ll be in the heart of Lincoln Park. In season, you’ll find the city’s best farmers’ market right there. And if you head two more blocks north, you’ll find Lincoln Park Zoo – one of the greatest free Zoos in the world.

Grab lunch or a cocktail at Café Brauer, right in the heart of the zoo. If you’re up for more exploring, head west a couple of blocks to Clark Street, then follow it back downtown through the historic Lincoln Park and Old Town neighborhoods.

2. Rolling on the river

Chicago’s Riverwalk is a must. Start at Michigan Avenue and stroll along the river. There are several cafes you can pop into, or better yet, grab a drink and a seat outside to watch boats, kayaks, and party cruises float by.  

While you’re there, sign up for Chicago’s famous architectural cruise for the inside story on dozens of landmark buildings. If you stay into the evening, walk to Wells Street for “Art on the Mart” – the world’s largest permanent digital art projection, illuminating the 2.5-acre façade of the Merchandise Mart with contemporary artwork. Pretty amazing – and free! 

3. Pizza two ways

Chicago is known for its deep-dish pizza, but here’s a little secret: locals are thin-crust people! Most only have a deep-dish when out-of-towners request it. One great option for tasting it is Lou Malnati’s, with locations across the city, but the best is the one right by the John Hancock building.  

For the ultimate experience, start with a cocktail at the restaurant on Hancock’s 95th floor – the views are unreal – then head to “Lou’s,” as Chicagoans call it, for a pie. If you’re a fan of Italian sausages, you’ll fall in love with Lou. 

For thin crust, Chicago shines. The best of the best is Vito and Nick’s, a South Side favorite since 1920. You’ll need a car to get there, but the city itself has dozens of thin-crust spots. Just ask your concierge for the closest one. (Insider tip: ask for the best “tavern-style” pizza – that’s what Chicagoans call thin crust.) 

4. A case of the Blues

Chicago has some of the best live music venues in the country, but it’s especially known for the Blues. The top spot to catch a set is Kingston Mines, on the North Side. With two stages alternating sets, the music never stops. It’s about a $10 cab or Uber ride from downtown and worth every penny. And if you’re more into Jazz than Blues, head to Andy’s Jazz Club, a downtown institution since 1951.

5. Skating the Ribbon 

If you’re visiting in winter, don’t miss skating “the ribbon” in Maggie Daley Park. It’s open from late November through March, with skates available to rent on-site. 

Whatever you end up doing in Chicago, you’re in for a great time – the city is as friendly as it is fun.