How to Experience the Best of Chicago in 48 Hours
Who doesn't love a weekend away, especially when it's a short flight from home? While New York, Los Angeles, and Miami may seem like obvious choices, Chicago is gaining traction as one of the hottest cities to visit this year, and for good reason—it's a quick flight away from most American cities, and it has a booming restaurant and art scene to boot.
The only issue: planning. Between the dozens of (more or less reliable) city guides out there and the late nights at the office that allow you to take a half-day off on Friday, there isn't much time to plan a quality itinerary. But fear not: If you want to get away but have not a single second to plan your trip, we've got you covered. We crafted the perfect Chicago itinerary to follow, even if you only have 48 hours in the city. All you have left to do is make a couple of dinner reservations. Start packing your bags and book a flight—these are the uncontested best things to do in Chicago.
Check in at the newly opened Kimpton Gray Hotel in The Loop. Centrally located and immaculately designed, this hotel will please the most discerning travelers. If you check in early and have a little free time, treat yourself to a treatment at Petrosino's, its in-house spa, or grab a drink at the hotel bar. You'll feel refreshed from your flight and ready to tackle the weekend.
For dinner, ride-share to Wicker Park to experience some of Chicago's best restaurants. Check in to Publican Anker for a more lively laid-back gastropub with craft beer and signature cocktails. For a slightly more upscale experience, make reservations at the Clever Rabbit, a vegetable-heavy restaurant in a stylish atmosphere serving fantastic cocktails.
The area is also lively with cocktail bars, so rally the troops for one last nightcap. Up & Up, located next to Publican Anker, is a rooftop bar inside the Robey Hotel and offers sweeping city views. If you chose Clever Rabbit for dinner and want something close by, head back in the direction of the Loop to Beatnik, a newly opened and acclaimed cocktail bar with serious boho vibes.
Because it's always 5 o'clock somewhere, slowly make your way to happy hour at Leviathan, a nearby cocktail lounge inside the Dana Hotel. Or if you would rather stop by your hotel room first, take a quick nap and refresh before heading out for the night. First stop: Proxi, a new restaurant and cocktail lounge in the West Loop.
Make room for dinner because Chicago's West Loop has some of the city's hottest restaurants, including Elske, a low-key spot perfect for date night offering a tasting menu of American fare in a Danish design setting. For something a little livelier, make your way to Girl & the Goat, a hot spot serving small plates in an open kitchen setting. Just make sure to reserve in advance.
The West Loop also has some of Chicago's best nightlife, so have that post-dinner espresso and head over to one of the many cocktail bars in the area. The Aviary is Alinea's answer to craft cocktails—if you're looking for a surreal experience. Finish off at the newly opened Blind Barber, a speakeasy-style bar located inside a shave-and-haircut shop.
Stroll in Style
You can't spend a weekend in Chicago without heading to the infamous Wrigley Field if there is a Cubs game happening. Start with a beer at one of the many local sports bars. Old Crow Smokehouse rooftop offers views of the stadium in a casual atmosphere and serves BBQ and Southern cocktails. Or head to Lucky Dorr, a newly opened bar serving local craft beers on tap. The name isn't a typo; the place is named after famed Wrigley Field groundskeeper Bobby Dorr.
If you have time for a full meal, head over to nearby Entente. The modern American restaurant just earned a Michelin star and serves a variety of high-quality dishes to surprise and delight.
If you only have a couple of hours to kill before your flight, head back to the Loop for drinks or a bite at Cindy's, a rooftop spot just a few blocks away from the hotel. Cindy's is known for its unbeatable views and delicious cocktails, and bonus: You'll have a prime view of "the Bean," in case you didn't make time to see it earlier in the weekend. There's simply no better way to end a perfect Chicago weekend.
And now, you don't have to be a tourist to visit these 10 attractions in Chicago.