If you love art and culture, parks and gardens, history and museums, or great food and drink, Chicago is your kind of town. Whether you have a trip to Chicago coming up or you’re looking for inspiration for your next getaway, you’ll find tons to love about the Windy City. From breakfast to dessert and everything in between, here’s what to do and where to stay in Chicago.

union station
Union Station.

Your Chicago Itinerary

First-time visitors, take note. Chicago is packed with major attractions like museums and parks as well as hidden gems like speakeasies and taco joints. It’s super easy to get distracted here, thanks to all the amazing options, so jot down a few of your top picks before you go to make sure you stay on track.

Dawn: Start With Donuts

Do-Rite Donuts kicks things off bright and early, and so should you. Don’t waste a single second navigating to one of this famous donut shop’s two locations, because these goodies are known to sell out quickly. The donut menu also changes daily, so you might find Candied Maple Bacon and Blueberry Crumb on the menu, or you might snag a Buttermilk Old Fashioned and a Pistachio-Meyer Lemon donut. Do-Rite has both vegan and gluten-free donuts, so everyone will find something to drool over.

Can’t handle sweets in the morning? That’s weird, but Do-Rite has you covered. Grab an inventive breakfast sammy like the Avocado with scrambled eggs and cheddar or the Bacon & Egg Donut Sandwich, which is exactly as mind-blowing as it sounds.

Field Museum
The Field Museum in Chicago.

Morning: Get Your Culture On

After the donuts have settled, it’s time to get your culture on. Plan to hit your pick of Chicago museums right when it opens so you can avoid the afternoon crowds. If you really want to be impressed, head to the Art Institute of Chicago, which is home to over 300,000 objects that span the entire history of art. This is a great spot to get a taste of everything, since it has design objects, architectural fragments from Frank Lloyd Wright, modern and contemporary art, ancient Greek ceramics, and much more.

If you love cutting-edge art, you’ll definitely want to set your sights on the Museum of Contemporary Art Chicago, which always has cool temporary exhibitions. The National Museum of Mexican Art is home to one of the nation’s top collections of Mexican and Latino art, and the Field Museum has everything from dinosaur skeletons and Egyptian artifacts to a Chinese rock garden and an exhibition on the history of tattoos.

Noon: Grab Some Tacos

Chicago is known for its deep-dish pizza, but unless you want to curl up and take a nap post-lunch, you’re going to want to grab something a little lighter. Tacos are always the answer, and Chicago has dozens of delicious options.

Big Star in Wicker Park is one of the biggest and most popular options, and it’s a good pick if you want to do a little day drinking with your lunch. Nearby, Antique Taco has an awesome century-old vibe with a contemporary menu that includes crispy fish tacos and meaty mushroom tacos. In Lincoln Park, Broken English Taco Pub dazzles taste buds with fun fillings like fried chicken. In River North, Seoul Taco gives classic tortillas a Korean spin.

lincoln park
Lincoln Park.

Afternoon: Enjoy a Breath of Fresh Air

After tacos, get ready to stretch your legs and work off all those tortillas. Take your pick of parks, green spaces, and waterfront promenades, as Chicago has the perfect spot for everyone. Want to take in some public art surrounded by skyscrapers? Head to Millennium Park and snap a selfie in front of “Cloud Gate,” the famously reflective sculpture.

If waterfront action is more your speed, head to the Milton Lee Olive Park and the adjacent Navy Pier, where you can ride some rides or get some great views of Lake Michigan. Or head north to Lincoln Park, where you can hang with the penguins in the free Lincoln Park Zoo or stop and smell the flowers in the Lincoln Park Conservatory.

Happy Hour: Sip the Coolest Cocktails

Next, wind down with a cool cocktail in one of Chicago’s best hidden gems. If you can find the Violet Hour, sip one of the speakeasy’s Prohibition era-inspired cocktails. If craft beer is more your speed, set your sights on one of the city’s many brewpubs, like Revolution Brewing in Logan Square or Goose Island on the Near West Side.

The Waterfront in Chicago.

Evening: Treat Yourself to an Amazing Meal

Chicago is home to some of the most amazing restaurants in the nation, so you’re definitely going to want to save room for a great meal. Go big at Alinea, which has a whopping three Michelin stars and a menu with out-of-this-world dishes that will challenge your concept of fine dining. If you can’t get in there, try Girl & the Goat, one of the most popular restaurants in town, where you’ll want to nosh on lamb rubs, tempura soft shell crab, goat empanadas, and confit goat belly. Be sure to save room for the caramel corn and malt balls.

If you get a second wind after dinner, rest assured that there’s plenty to do to keep you entertained. Catch a side-splitting comedy show at the legendary Second City or see one of your favorite bands at The Empty Bottle or Lincoln Hall.

Where to Stay in Chicago

Whether you’re planning a super short getaway to Chicago or you’re thinking about an extended stay in the Windy City, you want to make sure you stay in the perfect spot for you and your crew. Take a closer look at the top hotels, the best hostels, and the coolest private rentals in Chicago.

magnificent mile
The Magnificent Mile in Chicago.

Top Hotels in Chicago

Why book a stay at a massive chain hotel when you could snag one of the top boutique properties in Chicago? Check into the Kimpton Hotel Monaco Chicago and admire the decor, which takes its inspiration from the property’s former identity as a hat factory. You’ll find cool Victorian touches throughout, along with comfy beds and contemporary Midwestern food at the on-site South Water Kitchen.

Chicago is jam-packed with historic properties that boast tons of atmosphere, but The James Chicago is definitely a top pick. If you love mid-century modern-inspired furniture, ample natural light, and clean lines everywhere, you’ll appreciate this spot, which is just a block off the Magnificent Mile.

If you’re looking for a boutique spot with a slightly lower price point, try the Hotel Lincoln in Lincoln Park. This mid-rise hotel has tons of personality, with farm-to-table eats, a rooftop lounge, and even pet-focused amenities for your pup.

Best Hostels in Chicago

Book one of Chicago’s top hostels for the weekend, and you’ll be able to dedicate the majority of your budget to great food and fun attractions. Check out the Wrigley Hostel in Wrigleyville, especially if you’re planning to catch a Cubs game. This budget-friendly hostel comes with free breakfast, and it’s right around the corner from some of the most fun bars in town.

Located in the heart of Wicker Park, Holiday Jones is one of the hippest hostels you’ll find in the Windy City, and the low room rates are pretty amazing, too. You’ll find everything you need here, too, from free Wi-Fi and laundry facilities to foosball tables.

Located steps from Lincoln Park, the Chicago Getaway Hostel is a great place to rest your head without spending your entire vacation budget. Here you’ll find affordable rooms, along with cool perks like discounted museum tickets and tons of social events.

soldier field
Soldier Field.

Coolest Private Rentals in Chicago

When it comes to private rentals, it’s all about the neighborhood. After all, what better way to settle in and pretend like you live in a new city than grabbing a flat in one of the hippest neighborhoods in town?

If you want to be right around the corner from amazing coffee, awesome dive bars, and cute shops, set your sights on Wicker Park. It’s just northwest of the Loop and easy to access via the El, yet it feels like it’s miles away from the skyscrapers and steel that dot downtown. Make sure you’re within walking distance of Big Star, Wicker Park’s popular taco joint, and you’ll be golden.

You don’t have to be a fan of pierogi to fall head over heels for the Ukrainian Village, though that certainly wouldn’t hurt. This neighborhood, which is just south of Wicker Park, is home to great food, cool bars, and plenty of Eastern European culture. With tons of residential spots throughout this neighborhood, you can have your pick of private rentals, too.

Looking for a little more culture with your latte or craft beer? Head southwest to Pilsen, which is on Chicago’s Lower West Side. This cool neighborhood is home to the National Museum of Mexican Art and Thalia Hall, a hotspot for live music, making it a must for culture vultures visiting Chicago.

Ready to plan the best ever Chicago getaway? From hotels to attractions, design every aspect of your Chicago city break right here on GoDoTrip.