10 Things to Do on a Chicago Girls’ Weekend

From world-class shopping and dining to stunning architecture, Chicago is the perfect city for a girls’ weekend and one of my favorite cities. Here are my top 10 picks for things to do on a girls weekend, including restaurant and hotel suggestions.

View from LH Rooftop at LondonHouse

View from Cindy’s Rooftop

1. Visit Millennium Park & the Bean: If you haven’t visited Chicago before, you can’t miss this popular park and famous landmark (Cloud Gate aka the Bean). Join the millions of people who have taken a mirror selfie in the Bean.

2. Take the Architecture Boat Tour: Trust me, your group does not need to be architecture experts or even enthusiasts to enjoy this tour. It’s a great way to see the city from the water, and there is a bar on the boat. You can learn about Chicago’s history and stunning architecture, or just soak in the sun and enjoy the views.

3. Shop the Magnificent Mile on Michigan Avenue: The Magnificent Mile is a world-renowned shopping district featuring upscale retailers, luxury boutiques, and iconic landmarks.

4. Hit Up a Rooftop Bar: My favorites are LH Rooftop at LondonHouse and Cindy’s Rooftop. As shown above, LH Rooftop features river and city views, while Cindy’s Rooftop offers views of Millennium Park, the Bean, and Lake Michigan.

5. Stroll the Riverwalk: The riverwalk is one of my favorite parts about Chicago. There is plenty of space for a leisurely stroll or, for those looking for a more active activity, a run. It’s also lined with restaurants where you can stop by for a snack and/or drink. I loved the City Winery Riverwalk, which, in addition to wine, also offers beer and cocktails, but is only open seasonally.

Margarita at City Winery Riverwalk

Ceiling at Happy Camper in Wrigleyville

6. Visit Wrigleyville on a Game Day: Despite not being a huge baseball fan, I was pleasantly surprised by how much I enjoyed Wrigleyville, which is the area surrounding Wrigley Park, where the Chicago Cubs play. The restaurants and bars are well suited for a variety of crowds, not just baseball/sports fans. But you will certainly see lots of baseball fans on a game day. My favorite spot there was Happy Camper.

7. Enjoy the Beach: As someone who grew up in Maine, nothing is quite like the ocean. However, Chicago is right on Lake Michigan, which is about as close as you can get. There are sandy beaches, volleyball setups, and water sport and bike rental options.

8. Dance to Live Country Music at Bub City & Old Crow: If you like country music, you can’t miss Bub City. The live music was top notch (at least in my unprofessional opinion) and made for a great time.

9. Brunch is an Activity: Depending on your preferences, here are some great options for a girls’ weekend brunch:

• Drag Brunch at The River Kitchen + Bar, featuring (of course) a drag show, lively pop music, dancing, and hilarious commentary.
• 80 Proof, featuring an all-you-can-eat buffet, multiple floors, mimosa kits, and a DJ.
• The Hampton Social (River North), a less wild option featuring (softer) live music and a very instagrammable decor, including a greenery wall with a “rosé all day” sign.

10. Eat Some Pizza: My favorite restaurant in Chicago is Pizzeria Portofino. Although it has pizza on the menu and in the name, it’s not a typical pizza joint, and I viewed it more as a nice Italian restaurant with gorgeous views right on the river. A more laid back option is Parlor Pizza, where you can get a frozen espresso martini, which is dangerously good. Finally, I’m personally not a deep dish pizza person, but Chicago is famous for it. I haven’t been, but Giordano’s and Pequod’s Pizza are two popular options for traditional, deep dish pizza.

View from Pizzeria Portofino

Frozen Espresso Martini at Parlor Pizza

If you’re looking for hotel recommendations, check out the following:

• LondonHouse Chicago: I loved my stay at LondonHouse. We paid a little extra for a corner room suite, and had essentially the same views as LH Rooftop. It is right by the riverwalk and also makes trips to LH Rooftop (in the same building) very easy.
• The Hoxton: This one is on my personal bucket list. It looks beautiful, and it has a rooftop pool and rooftop bar. I tried to stay here on my last trip to Chicago but tried to book too late, and it was already fully booked. (Whoops! Hope you learn from my mistakes and book early!)

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– Kasey