When you think about one of the best spots in the U.S. that has it all—world class museums, a glittering skyline, Midwestern hospitality, eclectic neighborhoods and a progressive bar and food scene—Chicago is at the top of the list. There’s far more on offer than gusty drafts in the Windy City. In this Chicago City Guide, we’re exploring all the best gems to discover in the bustling metropolis on Lake Michigan.

Best Things To Do In Chicago

From the amazing architecture to a buzzing park on every corner, you’ll never lose inspiration because there are so many amazing things to see in Chicago!

Chicago’s First Lady Architecture Cruise and Architecture Museum

If you want the best views of Chicago’s amazing skyscrapers, you’ve got to take a river cruise. Because Chicago is an architectural feast, we had to take the First Lady Architecture Cruise. Aboard the First Lady, you’ll gain insight into the city’s popular architecture styles and the stories behind the most iconic landmarks. There’s a reason why this tour is top rated: in 90 minutes you get in depth narrative about the city’s foundations, and can enjoy a snack or drink from the breezy outdoor top deck. Afterward, head to the Architecture Museum to broaden your view of Chicago’s famous architecture.

Stroll the Riverwalk and Enjoy a Drink

Another wonderful way to enjoy the river and the city at the same time is to stroll the riverwalk. It’s amazing to be in the heart of the city and still find serenity and peace of the outdoors. Sip on a drink at a cafe and stroll along the riverwalk to enjoy a bit of nature in the city.

Navy Pier

When you’re in the heart of the hustle and bustle of the big city, it’s nice to have a place to escape to for some relaxation. Give yourself time to unwind at Navy Pier, a 3,000’ pier in Streeterville across from Chicago’s sparkling skyline. Here, enjoy a ride on the Ferris wheel, grab a meal from one of the many world-famous restaurants, or lounge shoreside with a treat and people-watch.

Visit Millennium Park and Take Pics at “The Bean”

Want to visit the world’s largest green roof? Then head to Millennium Park! This public park has one of the liveliest squares where locals gather and socialize. Additionally, public art is peppered throughout natural landscapes juxtaposing splashing fountains with architecture in one of the most interesting areas of Chicago.

This spot also happens to be home to Chicago’s most famous landmark: The Bean! You can’t visit Chicago without taking a selfie or having a mini photoshoot in front of this exquisite structure. Giggle at goofy reflections and distorted reality in arguably one of the most unique works of art anywhere.

Grant Park

You can’t visit Millennium park without visiting Grant Park… literally, you can’t, because Millennium Park is actually located within Grant Park. Encompassing over 300 acres, there’s a reason why Grant Park is considered “Chicago’s Front Yard.” This bustling community area features a million things to do and sea. You could easily spend your entire visit to Chicago exploring Grant Park.

Enjoy splashing fountains, visit the Art Institute of Chicago, or go with no agenda and enjoy getting lost meandering through this vibrant hallmark of Chicago.

Head to the Top Of The City For Amazing Views

Wherever you find yourself in Chicago, there’s bound to be a nearby spot to bask in the glorious views of the cityscape. Whether you have a drink at a rooftop bar or visit an observation deck for panoramic views, you’ve got to plan time to see the city from high heights boasting amazing views. Two amazing viewpoints are:

Skydeck at Willis Tower and John Hancock Observation Deck

The Skydeck at Willis Tower is a 110 story high skyscraper. From 1450 feet above the ground, you can only imagine how amazing this view is. Head to the highest building in the Western Hemisphere, where you can step out on a glass ledge and hope your knees don’t buckle. While it’s sure to send butterflies through your stomach, it’s an incredible experience and amazing way to fully grasp just how far Chicago’s highest point peaks.

Just 10 stories lower is the John Hancock Observation Deck. Technically, this building isn’t as high as the Skydeck, but from the top you can hardly tell the difference because 1,000 feet above ground is still high enough to take in breathtaking panoramic views of Chicago.

See a Show at Chicago Theatre

It’s hard to visit Chicago without drawing comparisons to the other big U.S. city: New York City, because there are many parallels. One of the best is that you can catch a Broadway show in Chicago at the famous Chicago Theatre. This landmark theatre encapsulates the heart of the city, with nightly comedy shows, musicals, broadway plays, orchestras and more. What’s more, the lavish French Baroque interior is adorned with stunning murals, and all the romantic elements of French architecture. Basically, you must catch a show at the Chicago Theatre if only to see this jaw-dropping architectural feast.

Gangster Tour

It’s impossible to write about Chicago without mentioning Al Capone, Prohibition and Chicago’s crime history. The best way to learn about all things 20s-30s Chicago is to take the Untouchable Gangster Tour. Learn about the scandalous exploits of famous gangsters and all the tumultuous events in Chicago’s roaring 20s crime era.

Hit the Shops at Magnificent Mile

Whether you’ve got cash to splurge or simply enjoy window shopping, Mag Mile a.k.a Michigan Ave has everything you’d want from a shopping strip. Spend a day shopping until you drop on this mile long strip. When your feet get tired dip into a restaurant for a meal, or hang on the nearby beach.

Where to Eat in Chicago

Chicago is famous for hearty comfort foods, but there is far more to eat in the Windy City than deep dish. Head to my guide for gluten-free dining in Chicago. In the meantime, let’s talk about some of Chicago’s best local markets, which are perfect for fresh and delicious meals.

Get the Chicago gluten free dining guide

French market

You’ll find tributes to all things France throughout Chicago. For a sample of French cuisine, head to the French Market. Stroll through the many food stalls for fresh produce, grab and go eats and novelty stalls. If you aren’t gluten free, you can tear through the French Market and sample everything on offer. But don’t sweat if you are gluten free, Flip Crepes has you covered with delicious, 100% gluten free crepes. Bon Appétit!

Fulton-Randoph Market District

One amazing thing about Chicago is that, despite the amazing historic sites, there’s always new and emerging scenes. One such is the Fulton Market, an innovative culinary arts area for progressive and avant garde restaurants and cafes. Now located on the Near West Side, this former meatpacking and industrial district is now a modern area thriving in tech, restaurants and hip new hotels.

Where to Drink - Best Bars in Chicago

Cindy’s Rooftop

You can’t visit Chicago without heading to the gem that is Cindy’s Rooftop. Bottom line, Cindy’s is the top dog for rooftop bars in Chicago. Located in the Chicago Athletic Association Hotel thirteen stories above Millennium Park, enjoy views of Lake Michigan, historic architecture and classic libations from this iconic rooftop terrace.

Coq D’Or

Nestled cozily inside the historic Drake Hotel, this 1930s bar Coq D’Or encapsulates the soul of Prohibition-Era Chicago. Head here for underground speakeasy vibes and traditional drinks with a modern spin.

Legends for Blues

Muddy Waters and Buddy Guy are two of the great blues musicians to emerge from Chicago. For a look at Chicago blues history, head to Buddy Guy’s Legends, a classic blues club combining cajun food with nightly acts in a delightful and welcoming club. Sip on a martini, listen to local musicians and let your blues melt away.

Where to Stay in Chicago

Because Chicago is a big city, you’ll want to stay in a central location that’s footsteps from all the best sights and attractions in downtown. I personally like to stay at interesting hotels that have a unique history and design. That’s why I chose to stay at StayPineapple, an iconic boutique hotel in The Loop that combines beautiful architecture and design with a complex mob history.

During prohibition, Al Capone’s narcotics supplier was a dentist whose office was located in the formerly named “Reliance Building.” In 1929, the dentist was shot to death by Capone’s gangsters in room 809 of what is now Staypineapple. Mob history is a huge part of Chicago’s history, so staying at a hotel that’s a beautiful historic landmark was a really unique experience! The historic world-class architecture is awe-inspiring, and the interiors are oozing with charm via marble ceilings, mosaic floor tiling, iron gates and stairwells and basically the most amazing interior design in Chicago.

No matter where your trip to Chicago takes you, you’re sure to have an amazing experience! What’s your favorite spot in Chicago?

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