Chicago’s outdoor attractions, restaurants, parks, bars, and more are currently open with new safety precautions. As the city has a re-opening plan, you can help support so many great businesses while planning your next weekend getaway. Do you only have time to visit for a quick weekend? Here’s my 48 hour weekend in Chicago, where I will be sharing the best places to eat, drink, and play. 



I’d recommend starting your Friday afternoon bar side at Federales. Not only is this a youthful bar, but the lively atmosphere is so exciting. Are you a tequila fan? This will be your new favorite spot. Make sure to order your tequila shot in an ice shot glass. Outside, they have a bell to throw your ice glass at after taking the tequila shot. It’s enjoyable for a group of friends. 

Evening Booze Cruise

While it’s currently winter, I highly recommend in the spring, summer, and fall taking Booze Cruise on the Chicago Harbor. I went to Eventbrite to find deals and recommendations. I ended up choosing a sunset cruise. It was only $20 per person, and each drink was $5! It was lovely getting such an incredible view of the city; plus, extremely affordable. 

Pinched On The River
Pinched on the river | Chicago Pinched on the river | Best places to eat and drink in chicago | 48 hour weekend in Chicago |

I cannot express this enough…you NEED to visit this restaurant if you enjoy Mediterranean food. Not only did they have an entire gluten-free menu, but all my friends and I agreed that it was one of the best restaurants I had ever been to. It’s very casual but so quaint. We sat outside near the river with twinkling lights above us and a fabulous bottle of wine to pair with our dinner. This eclectic menu was one I will visit again. 

Extra Information: This restaurant is nestled down the street from Navy Pier.

Bar Close: Because of the COVID restrictions, when I was in the city, all bars and restaurants closed at 10:00 PM. Make sure to research this before your trip!


Homeslice for Brunch
Homeslice | Chicago homeslice | Best places to eat and drink in chicago | 48 hour weekend in Chicago |

Go to their website. Yes. Go there now. You will be drooling over the delicious brunch and full food menu. Not only is the menu literally to-die-over, but the cocktail menu is equally as fabulous, and the Bloody is one of Chicago’s best! I had a gluten-free breakfast pizza, which was amazing. The atmosphere is so vibrant, fun, and beyond unique. It was a favorite of the weekend for sure.

Utopian Tailgate
Utopian Tailgate | Chicago Utopian Tailgate| Best places to eat and drink in chicago | 48 hour weekend in Chicago |

Hello, jungle gym for adults! This rooftop bar not only has a fantastic view of the city but has chill vibes and knows how to create a party-type atmosphere. Each group of chairs/seating has tons of different drinking games you can choose from, a tire swing, an outdoor and indoor bar, and more! Not only is the atmosphere perfect for a sunny Saturday, but their cocktail menu is beyond spectacular…such unique options! The fun will never end at Utopian Tailgate.

Murphy’s Bleachers
Murphy's Bleachers | Chicago Utopian Tailgate| Best places to eat and drink in chicago | 48 hour weekend in Chicago |

Any sports fans out there? This bar is actually across the street from Utopian Tailgate, so it is just a quick walk away. I went to Iowa State University, so this bar is known for playing Iowa football and is owned by an Iowa State alumn. The bar has a cool outdoor/backyard patio and knows how to make a hearty drink. 

Only have time for a 48 hour weekend in Chicago? Make sure to check out these bars and eateries as they were my favorite!