I absolutely adore having my girlfriends visit the city. Boutique hotels, endless brunch options, and unlimited Instagram-able spots, Chicago is the perfect destination for a weekend for the girls. With so many options in the city, I thought it would be fun to create an ideal itinerary.
Grab your girlfriends and head on over to the Windy City!
Day One:
Check into your hotel as soon as you arrive. Time to unpack and let the girls weekend begin. If you are like me, you’ll want to stay at a boutique hotel with a killer bar.
- The Robey. Located in Wicker Park, The Robey is brand-new and has been making quite a name for itself (read about my experience). Grab a quick drink at the bar, located on the 13th floor, while enjoying an incredible view of the city.
- Hotel Lincoln. A cute hotel in Lincoln Park located right on the park. Make a stop at the rooftop bar, the J. Parker, before going out for the night.
- Chicago Athletic. One of my favorites in the city, the Chicago Athletic Association is a one-of-a-kind experience. In my opinion, Cindy’s is the best rooftop bar in the city. Soak in views of Millenium Park with a dirty martini.
Once the cocktails are finished, it’s dinner time. The West Loop is perfect for hopping around with girlfriends. No matter what restaurant you end up at on Randolph, you’ll have a great meal (Need ideas? Bad Hunter, RM Champagne or Parlor). After dinner, take time to walk the strip. Lone Wolf has a cocktail for everyone and Bar Siena makes the classics incredibly well.
Day Two:
Hit the snooze once (or twice) before rolling out of bed for the first item of the day – a workout class! As you know, I am a Soul-Cycle fanatic, but Aerial fitness is entertaining with friends. If there’s a workout class you’ve always wanted to try, Chicago will have it.
After showering and a quick stop at your hotel, head over to Restoration Hardware for a brunch/lunch at Three Arts Café. Long line? Grab a cocktail or a coffee at the bar and explore the five floors of #housegoals.
The downside of having so many options is having so many options. You can fill the afternoon with shopping, a spa day, exploring art museums, an afternoon show (see a quick guide here) or booking a trip on the Chicago Architectural boat tour.
Working up an appetite, it’s dinner time. I recommend figuring out another neighborhood to explore and making dinner reservations accordingly. Don’t worry – I’m providing options:
Laid back – Big Star / Park and Field / The Hampton Social (known for the Rosé sign) / Happy Camper / Parson’s Chicken & Fish
Formal – RPM Italian / Maple & Ash / Café Ba-ba-reeba / Ada Street
Day Three:
First thing on today’s agenda? Brunch. Beatrix, an American eatery, is my go-to for all things delicious. Fresh juice (with alcohol) is my hangover cure, and luckily, they have plenty.
Tummies full, head down to the river walk to enjoy the rest of the afternoon with a glass of rose at City Winery. As the summer approaches, more restaurants will open along the path. Grab a seat, enjoy the people watching and the boats passing by. This is a great way to wrap up the weekend, before heading to the airport.
Staying longer? Want more recommendations?
Nothing like a classic Chicago dog at Shake Shack. Don’t forget the cheesy fries!
Need a sugar rush? Bombobar / Stan’s Donuts / Molly’s Cupcake / Doughnut Vault are the obvious answers.
Have a sweet tooth? Head to Dylan’s Candy Bar for something for the sweet tooth.
Looking for a cute boutique? Head to Lincoln Park (Halsted and Armitage) or far north to Andersonville and you’ll be able to find something you love.
More brunch options? SohoHouse / Little Goat Dinner / Ralph Lauren Café
Ultimate girls weekend activity? Book an appointment at DryBar.
Most importantly, don’t forget the deep dish! #pizza
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