A girls weekend in Chicago is the best way to spend a weekend in the city, especially in the summer. With picture perfect restaurants, drinks with a view and endless outdoor activities, let’s start planning your next girls trip to Chicago.
My one word of advice: Do your best to explore as many neighborhoods as possible! One of the best parts of the city is the various neighborhoods with VERY different personalities. Chicago is easy to navigate (it’s a perfect grid system), public transportation is safe and clean, and there’s always a Divvy bike station to be found (for a fun mode of transportation).
Where to Stay in Chicago:
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Hoxton Hotel, 200 N Green St. Located in the West Loop, the Hoxton is one of my new favorite hotels. If you are a foodie, this location is prime! The hotel is located near some of the best restaurants in the city (all within walking distance). The lobby has one of the cutest coffee/cocktail spots and Cabra (see below – located on the rooftop) is one of my favorite dinner spots.
Chicago Athletic Association, 12 S Michigan Ave. If you are a history nerd (like me) or love architecture, this is the hotel for you. Built in 1893, this building is a landmark among the Chicago skyline. Each room is decked out in an old-school sport vibe and you’ll see the theme carried throughout. Make sure to take advantage of preferential entrance for the rooftop if you are a hotel guest!
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Aloha Bangtel, 1478 N Milwaukee Ave. One of my most recent discoveries, this place looks beyond adorable for a girls weekend. Picture perfect rooms, lots of space and a fun location in Wicker Park, this place is a great alternative to your traditional hotel stay.
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Splurge: The Peninsula, 108 E Superior St. Located right off Michigan Ave, this hotel might be my favorite in the city. The service is impeccable, the restaurants delicious and their spa is one of the best in the city. When I need a cocktail with a view, I head to Z Bar at the Peninsula.
Where to Eat in Chicago:
Beatnik on the River, 180 N. Upper Wacker Drive. Can whoever designed Beatnik please come help decorate my home? This Moroccan-esque decorated space is a great place to rest your feet after a day of shopping or sight seeing downtown.
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Parson’s, 2952 W Armitage Ave. Fried chicken sandwiches and alcoholic slushies. A combo you probably didn’t realize you were missing in your life. Parson’s has one of the most spacious outdoor patios in the city. A great spot for a lunch pit-stop or an early start to your evening plans.
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Blue Door, 52 W Elm St. It’s easy to escape the hustle and bustle of the city at Blue Door Kitchen. Their patio is easily one of the most magical and quaint outdoor spaces I have found in the city. It will transport you to the French countryside. I love ordering one of their delicious salads, ordering a bowl of fries for the table and pairing it with a crisp glass of rosè.
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Etta, 1840 W North Ave. Etta is one of the newest restaurants I have added to my “favorites” for out of town guests. Their brunch is EXACTLY what you want after a night of one too many drinks. Do yourself a favor and order a plate of pancakes for the table and pair it with one of their delectable brunch cocktails (and a coffee).
Pizzeria Portofino, 317 N Clark St. A true oasis on the Chicago riverwalk. Order a cold bottle of wine, pizza for the table, and enjoy the people/boat watching from the comfort of your seat. It doesn’t hurt that the restaurant is aesthetically designed for the perfect group photo.
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Cabra, 200 N Green St. My mouth is already watering thinking about Cabra. If you and your friends consider yourselves “foodies,” then be sure to snag a reservation here. A creation of Stephanie Izard’s (think Top Chef), you won’t be disappointed by anything on the menu. Their Peruvian cocktails are *chef’s kiss.* Located on the top floor of the Hoxton Hotel, get here early and enjoy a drink with a view.
Where to Drink:
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Restoration Hardware, 1300 N Dearborn St. I could spend hours here. Grab a glass of champagne and enjoy exploring the many floors of luxurious furniture and plan out your “dream home.”
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LondonHouse, 85 E Wacker Dr. While I don’t typically like recommending a place solely for the views, in this case I will make an exception. Grab a drink (or two) and soak in the views of the Chicago River.
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Park & Field, 3509 W Fullerton Ave. This patio translates well from day to night. Spend a morning here for brunch or head here after dinner to enjoy the fire pits and a night cap. Great for a larger group with plenty of room to spread out!
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Cindy’s Rooftop, 12 S Michigan Ave. The views of Millennium Park are unmatched. The bar can get SUPER crowded on the weekends, so be sure to head here early. I usually grab just one drink before dinner reservations downtown.
What to Do in Chicago:
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The Riverwalk. One of the greatest additions to the city, you’ll find bars, restaurants and lots of outdoor space along the Chicago River. I recommend enjoying a glass of wine from City Winery while boat watching.
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Jeni’s Ice Cream, multiple locations. If you have a sweet tooth, this is your spot! There’s nothing better than grabbing a scoop (or two) of one of Jeni’s famous flavors after dinner. Lucky for you there are plenty of locations around the city!
Rent a boat. One of the best ways to see the city is by boat. Whether it’s a pontoon, a speedboat or sailboat, there is something for your group. You can also hire a captain, so you can enjoy the incredible views with a drink. I have had a lot of luck in the past with Boatsetter.
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Farmer’s Market, multiple locations. One of the best ways to spend Saturday morning is at the Green City Market in Lincoln Park. Grab a coffee, some fresh flowers, and enjoy the live music and the plethora of food stalls from the surrounding area.
Where to Shop:
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Alice & Wonder, 956 W Webster Ave. The cutest store front. I always want to buy everything in this store! Be prepared.
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Lost Girls Vintage, 1947 W Chicago Ave. If you are looking for an incredibly curated selection of vintage clothing and items, this is your spot!
Note: At this time, I would encourage you to do your research as many restaurants, bars and hotels are changing their hours and experiences due to COVID-19.
Hopefully I’ve provided you a starting point for planning and if you need more ideas, check out my original post here. As always, feel free to reach out to me with any of your trip questions or more recommendations! Enjoy the city!
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