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The Ultimate Guide To A Weekend in Chicago

Chicago is one of those cities that turns getting lost into not only an art form, but an incredible adventure. A sprawling city with many neighborhoods that still maintain that old school urban vibe, Chicago is bustling with amazing restaurants and bars, cool event spaces, breweries galore, an art scene that’s pretty impossible to conquer in just a weekend, and a whole lot of history and character.

Rather than booking the cliché trip to Vegas for a bachelor party, or to Sonoma for wine tasting with a bachelorette party, you may want to consider adding this great old American city to your list of weekend getaway possibilities. There are party spots in every neighborhood, whether you’re looking for a great bar to have a seat and unwind from a day of sightseeing, a restaurant with food as good as your grandmother’s, or a warehouse space to throw an epic party.

Oh, and be sure to stop by Millennium Park if you get a chance, it’s truly impressive and packed with tons of cool art installations. The Museum of Contemporary Art and The Field Museum are also worth a gander if you’ve got the time. So much to see!

Reporter: Alyssa Brown
Photo: Jill Tiongco
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A New Leaf

Chicago, Illinois
Opened by a floral design crew, this industrial venue would be an epic place to throw a private event with your best friends. Maybe have a caterer come through for a sit down dinner, or arrange some kind of classes with a sommelier. With two levels of exposed brick and a crush-worthy courtyard, New Leaf is also great for pop-up events.
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Cindy's Rooftop at Chicago Athletic Association learn more

This popular rooftop bar might be one of the best places to enjoy sunset cocktails overlooking the harbor prior to a night out in the city. They’re open late night too, which could be fun for a nightcap if you’re about that party life during a celebratory weekend. Did we mention it’s gorgeous?
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Photo: The Allis
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The Allis

​Chicago, Illinois
Set in the Soho House lobby, this 1907 space is insanely beautiful. Whether you go for afternoon tea, breakfast, brunch, or an after-work drink, The Allis is so extravagant and impeccably maintained you’ll think you’ve landed in another time period. Go with the ladies, stay long enough to exchange a few great stories.
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Maude's Liquor Bar

Chicago, Illinois
Contrary to its name, Maude’s is known for more than the cocktail list. Cassoulet and other fancy french foodie finds are all the rage at this gorgeous little spot. Pile into the banquette seats with your nearest and dearest and be prepared for a night of good eats!
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Dove's Luncheonette

​Chicago, Illinois
Nothing like a little Tex Mex in a retro diner setting to totally reset an exhausted crew of bachelor party dudes. With counter seats and a jukebox, this lunch spot is as charming as it is delicious. Check it out when you’re in dire need of some queso.
Photo: The Bristol
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The Bristol learn more

Handmade pastas, charcuterie boards, and loads of vino options flow at this Bucktown restaurant. This would be a great place to do dinner with the guys during a bachelor weekend. Plus, there’s a private event space if you’re worried about rolling through with a rowdy crowd.
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Photo: Trenchermen
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Trenchermen

Chicago, Illinois
Back in the day, this modern gastropub was a Russian bathhouse. It's now one of the best brunch spots in Chicago. The décor is masculine and the food is baller. Plus, they have small private room that would be great to book if you’re looking for a little extra privacy for your crew.
Photo: Big Star
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Big Star learn more

Big Star is about as down-home as it gets. Sitting on the patio with margaritas and guac almost makes you feel like you’re in Austin just hanging out on the sidewalk. But, this is Chicago, so it’s that much better (wink wink). Check out this spot for a late lunch or a snack on the go with your buddies.
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Owen + Alchemy

Chicago, Illinois
Call us crazy, but when we’re feeling under the weather from too much partying, a good green juice always makes us feel more balanced and rejuvenated. This chic juice bar slash apothecary is a perfect place to pop-in during a bachelorette weekend to get everyone a healthy little pick-me-up.
Photo: Milk Room
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Milk Room learn more

This prohibition style bar is perfect for a bachelor party crowd. Set inside the Chicago Athletic Association’s dark and brooding drawing room area, this was an actual speakeasy back in the day. Book ahead to scoop up one of the eight seats at the bar.
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Photo: Salvage One
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Salvage One learn more

This massive prop shop and warehouse has a courtyard that would be amazing for throwing a pop-up dinner party outdoors. We could totally see Salvage One being transformed for an unforgettable night of celebrating a bride or groom to be. Plus, there’s no shortage of one-of-a-kind antiques and props to decorate the space with.
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Giant

​Chicago, Illinois
Sure to please your artsy friends with its cool collection, Logan Square’s Giant is one of the top restaurants in Chicago right now. Check this spot out if you’re traveling with a crew of foodies who like a modern atmosphere and a full belly.
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Photo: Alan Shortall
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$269 avg. room rate
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Chicago Athletic Association Hotel learn more

This late 19th century athletic club reopened as a hotel that’ll make your head spin from all the detail ogling you’ll find yourself doing once inside. The designers did an incredible job of layering modern furnishings into a space that’s rich in history and architectural detail. If you’re not able to swing rooms here, at the very least you should stop by to check out the lobby area and one of the many top-notch bars.
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Photo: 3 Arts
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3 Arts

​Chicago, Illinois
Admittedly, this place has full potential to be totally weird, as it’s located inside of Restoration Hardware. But, it’s actually anything but weird. This epic warehouse slash atrium space has a monstrous glass ceiling that gives off all kinds of warm vibes. Brunch, lunch, or dinner here would be really fun with a group of ladies who appreciate a great ambience.
Photo: The Publican
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The Publican

​Chicago, Illinois
The oyster bar at The Publican is two things. One: beautiful. Two: packed. This is THE destination for oysters in West Loop and it’s got enough other options on the menu to keep all your friends enthused. The setting is light and airy, while the food is big on seafood and pork.
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The Guesthouse Hotel learn more

As if the historic neighborhood weren’t enough of a reason to check out the Guesthouse Hotel, it’s really got some of the nicest hotel rooms in Chicago for large groups. You can rent a one, two, or three bedroom suite, so consider this ground zero for getting the bachelorette party started.
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Photo: Collin Hughes
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Bang Bang Biscuits and Pie

​Chicago, Illinois
So, malted milk chocolate pie is a thing. Yep, wish we came up with that on our own, but the geniuses over at Bang Bang have it covered. These guys make some really incredible Mid-West style comfort foods, from brisket biscuits to buffalo chicken pot pie. Don’t say we didn’t warn you to wear your stretchy pants.
Photo: The Beer Haul
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Revolution Brewing

​Chicago, Illinois
You’ve probably heard of Revolution Brewery and maybe didn’t even realize it was from Chicago, but this Logan Square beer spot makes a really fun and interactive stop during a weekend in the city. The beers are all fantastic and made with love, and the space itself is great for a group.
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Summer House Santa Monica

​Chicago, Illinois
Love, love, love this Summer House for brunch with the gals. The light and airy space has us wanting to spend a few hours sipping bubbly and cackling with the best of them. The food is all light and fresh, with quinoa salads and the like. Truly, we’re always fans of spaces filled with tons of natural light.
Photo: Revel Room
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Revel Room

Chicago, Illinois
Hello, bachelors! This spot has that masculine, refined air about it that you’d expect to find in an old gentlemen’s club back in the day. If you’re a fan of Chicago history, this is the spot for your crew to throw back some cocktails and laugh about the good ole days.
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Monteverde

​Chicago, Illinois
Two words for you about this place: handmade pasta. Also, you’re welcome. Monteverde is one of the best Italian restaurants in Chicago and they’re great with group dining. Check it out for dinner and be sure to order family style to get a taste of everything. You won’t regret these carbs!
Photo: Anteprima
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Anteprima

​Chicago, Illinois
Anyone who grew up with a Nonna can appreciate this total old school Italian gem of Andersonville. This is one of those places that makes you feel immediately at home because of the authentic cooking and simple décor. Check it out for a group dinner if you’re looking for incredible Italian food in a cozy setting.
Photo: Au Cheval
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Au Cheval

Chicago, Illinois
You’d be hard pressed to find a list of restaurants and bars in Chicago that didn’t include Au Cheval. This burger spot also has awesome cocktails, so consider this a perfect place to stop if your crowd needs to fuel up and catch a good drink too. Think industrial cozy vibes in the most delicious way.
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Maria's Packaged Goods and Community Bar

​Chicago, Illinois
But you guys, this might be one of the cooler breweries we’ve seen in a while. Check out the rad architecture, sip on beers and bevs, unwind and enjoy vacation with your friends. Maria’s is the kind of place that’ll have you instantly talking about opening up your own brewery with your buds.
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