While sandy beaches and tropical hotspots are a go-to for winter vacations, there’s one midwestern city that deserves just as much attention.

Filled with museums, award-winning restaurants, local breweries, fantastic shopping and more, Chicago is the perfect stop for a weekend getaway all year round. But over winter there is something extra special about the way the skyline lights up and the city’s neighborhoods come to life.

In fact, there is SO much to do in this city that it can be hard to narrow down the favorites. After all, that’s one of the best parts about Chicago—there is something new to savor and explore for everyone. No matter what you’re into, here are the top things you should add to your itinerary for a  weekend trip to the 312.


Deep dish pizza

If you love pizza then you’ve probably already heard of Chicago deep dish. And if you haven’t heard of it, you should definitely check out this Chicago fixture. Thick, golden crust filled high with cheese, toppings and tomato sauce—there’s nothing like it, especially over winter. Stop by Chicago classics like Gino’s East, Uno’s or Lou Malnati’s. Just remember to come hungry!

West loop restaurants 

Between Randolph’s restaurant row and the booming Fulton Market District, there’s too many amazing spots to list. Whether you’re looking for a celebratory dinner, hot spot, foodie experience or just a taste of Chicago nightlife—this area has it all. We’re talking Stephanie Izard’s Girl and the Goat, local favorite Kuma’s Corner for burgers and metal music, upscale cocktail bar The Aviary or Kaiser Tiger for beers and curling.

Local breweries

Chicago’s local brewery scene has really taken off over the last few years. From sours to double IPAs to barrel-aged stouts and seasonals, there’s a pint for everyone. In fact, you can find a taproom or brewpub to pull up a stool at in almost every neighborhood. With two locations, Half Acre features classics and experimental options to satisfy all parties. For an upscale brew experience, check out Moody Tongue Brewing Co. And you can’t forget Revolution Brewing, whose Logan Square brewpub has an awesome menu to go with your beers.

Weekend brunch

It’s hard to name one single spot for where to go for brunch in Chicago. Thankfully, you have two days to enjoy that in-between mealtime because this city takes brunch seriously. Warm and gooey cinnamon rolls, build your own omelette stations, breakfast bread pudding, fried green tomatoes, chicken biscuits—is it brunch time yet? Here’s a quick guide to the best brunch spots in every Chicago neighborhood.

Chicago Restaurant Week

If you plan on visiting Chicago anytime between January and February each year, then check out the menus of Chicago’s Restaurant Week. Featuring around 400 downtown and suburban restaurants, Restaurant Week offers diners special prixe fixe menus. These menus may feature stars of that establishment or it could be an exclusive menu just for this 17-day celebration of Chicago’s food scene. Check out the list of restaurants participating here.



One of the best parts of a bigger city is the shopping—and Chicago delivers. For luxury stores, pop-ups and department stores, head to Magnificent Mile (or Michigan Avenue) for the city’s premiere shopping strip. People travel from all around the world to shop this mile-long stretch of shops, like The American Girl shop at Water Tower Place. If you’re looking for local boutiques, head to Wicker Park or Lincoln Park for less traditional but just as swoon-worthy options.

Ice Skating

Over the summer, you’ll find Chicagoans running and playing and lounging in city parks located throughout the city. But during winter, the city takes the opportunity to turn a few of those parks into ice skating rinks. You can find one in Wrigleyville, next to the Lincoln Park Zoo or over in Millenium Park at the center of everything. (Travel Tip: You can save on skates when you stay with Hilton.)


On chilly winter days, museums are a perfect, indoor escape for visitors and locals alike. And the good news is, there are quite a few museums to choose from. Some of the top choices include the Shedd Aquarium for underwater lovers, the Art Institute of Chicago (a true Chicago treasure) for art lovers and the Field Museum for history buffs.

Live entertainment

Chicago is full of amazing venues, theaters and talent. Just like when it comes to picking a spot to eat, it can be a challenge to decide on what to see—because everything is just THAT good. Hit up a concert at the iconic Green Mill Tavern. Have a laugh at The Second City comedy club. Or catch a Broadway show, performance or play at the legendary and stunning Chicago Theater.


LondonHouse Chicago, Curio Collection by Hilton

With a chic rooftop bar and views of the Chicago River, the LondonHouse is a great option for those craving style and affordability. Did we mention it’s also steps away from Magnificent Mile and great shopping?

Palmer House, a Hilton Hotel

This Chicago landmark hotel is surrounded by well-known attractions like museums, theaters and State Street shopping. However, between the rich history, lush interiors and relaxing spa, you may just want to stay in.

Hampton Inn Chicago Downtown West Loop

Whether you’re visiting for work, a girl’s trip or family vacation, this Hampton Inn lets you stay right downtown without having to splurge. Plus, we already mentioned how Chicago’s West Loop neighborhood is full of amazing dining spots which is sure to sweeten your experience!

Waldorf Astoria Chicago

For those looking to treat themselves, there’s no better option than the Waldorf Astoria Chicago. Located right downtown, you’ll be surrounded by premiere shopping streets and dining spots. Plus, there’s a spa on the premises for those looking to just relax with the royal treatment.

If you want to explore even more places, Hilton has you covered. With over 20 hotels downtown and over 90 more in the entire Chicagoland area, there’s a perfect spot waiting for you!


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