S+W Travels | 24 Hours in Chicago, IL

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Last weekend I made the short jaunt to Chicago to see one of my best college friends and enjoy big city life for a few days. Our must must dos included: Comedy | Art | Doughnuts | Craft Cocktails | City Views | a Good Cup of Coffee | Portillos or a Deep Dish Pizza.

Chicago is a bold city. It’s full of warehouses, factories, and old, brick buildings that have been revitalized into urban chic. And some of course that have stood the test of time, but with battle scars of graffiti and abandonment. It adds to the character. The skyline is spectacular and Lake Michigan is a beautiful backdrop. Being the third largest city in the US, it can be overwhelming, but the heart of the city is cozy, walk-able, and very public-transportation friendly. It has many different neighborhoods, each boasting their own claim to fame. It’s on old city, rich in industrialized history. You could easily spend a week here to truly get a sense of the city and what it has to offer.

We only had 24 hours to really soak in the city. With such a short trip, we focused on one or two highlights, a good spot to stay, and then filled in the rest with food, drinks, and shops in the area. With shorter trips, it’s smart to focus on one neighborhood, otherwise you’ll be wasting all of  your time and money on Ubers. We spent most of our time in the River North neighborhood and easily walked everywhere we went (with the exception of two cab rides). 

11:00 a.m. – You made it to the city! We took a train from the burbs and arrived at Union Station to meander the city and around the river to our first stop, Intelligentsia Coffee. It’s a 1 mile walk from Union Station and right next to Cloud Gate (aka the bean)Go for a latte to go as it’s typically busy, but their latte art is beyond impressive and totally instagram worthy.

12:30 p.m. – Drop your stuff at the hotel. We stayed at the Freehand which we loved (call ahead to ensure an early check in). It had exactly what we wanted in a hotel: centrally located, great accommodations, onsite food, coffee, and cocktails, and budget friendly. Half the rooms are shared, bunk-up style rooms with the remaining being private accommodations, but with a boutique hotel feel; each space was expertly decorated. It gave off a comfortable, worn in vibe meets industrial feel with smooth leather seating adorned by Southwestern tapestries, succulents, rich colors, concrete, tile, and modern amenities. They also feature several fun events planned onsite for guests: live music, walking tours, etc.

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1:00 p.m.: Just around the corner from the Freehand, grab lunch (or drinks and snacks) at Cantina Laredo. We happened to be there on a Sunday where brunch is served until 3:00 p.m. Upon arriving, we were greeted with a steaming heaping pile of fresh tortilla chips and two varieties of house salsa – each with a unique twist beyond the familiar tomato-cilantro-onion combo. We couldn’t pass up the table-side guacamole (worth it) and then absolutely stuffed ourselves with our entrees. Each brunch entree comes with a mimosa or bloody maria, a side of Mexican potatoes, and a churro-like cup with fruit inside. You will not leave hungry. The Chilaquiles were fabulous and they’re known for their margaritas.


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2:30 p.m.: Walk off that gauc and head the 0.8 miles to the Museum of Contemporary Art. The collections are impressive and offer more room for interpretation than many exhibits I’m used to. They provided just enough background and artist information to give a foothold, but they don’t tell the story. I especially loved their timely “Run for President” exhibit by Kathryn Andrews which explored how advertising, presidential campaigns, and other productions of mass appeal affect society and in turn society effects how campaigns look and act based on their true meaning.

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4:00 p.m.: Grab a cab or an Uber from the Museum and head to Judy Maxwell Home, an adorably quirky gift shop and home goods boutique. Great paper goods, Chicago souvenirs, and cheeky home & trinket items.

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5:00 p.m.: Right across the street is Pomp and Circumstance, perfect for a cocktail or two. An impressive drink menu set among a library-meets-exposed-lighting-meets-plaid-upholstery-meets-mismatched-china setting, it also has a full menu for snacks.

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Also nearby: if $13 cocktails aren’t your jam, try the burger and beer joint, Woodie’s Flat.

6:30 p.m.: Time to head to The Second City for a comedy show. The acting, jokes, and setting were all quality and genuinely funny. Second City is famous for it’s impressive alumni (Steve Carell, Tina Fey, Amy Poehler, etc.) so it was fun to see the talent with the possibility they may be the next big, funny thing.

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10:00 p.m.: From Second City, you’ll want to take another cab back to the River North area (a $7 cab ride) and before calling it a night, check out Three Dots and a Dash, an almost hidden vintage Tiki Bar. Upon entering the back alley doorway, you’re greeted by a wall of skulls and traditional totem poles. The bar is seating only, and low tables are among the grass bar, low lighting, and vintage island flair. Authenticity rules. Servers are clad in island garb, drinks are served with garnishes that make paper umbrellas look tacky, think instead of dolphins made from bananas, hibiscus flowers, and drink stirrers shaped like flamingos. The drinks are fresh and many feature stunning special effects. My favorite was the Bunny’s Banana Daiquiri.

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12:00 a.m.: Luckily Three Dots and a Dash is right around the corner from the Freehand and a very safe and easy walk back (unless you’re by yourself, then obviously, use a cab).

9:00 a.m.: Your first stop today should be doughnuts. Grab a coffee from the Freehand folks at Cafe Integral and make your way to the best fried dough you’ve had in a while. Doughnut Vault, has four offerings – their buttermilk doughnut, gingerbread stack, glazed, and a flavor of the day filled. The Chestnut glazed doughnut was light, airy, and enclosed in a perfect sweet level glaze with a slight crisp to it so when you bite into it, it immediately melts in your mouth. Firecakes and Stan’s Doughnuts are also close by and great choices.

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10:30 a.m.: Pack up your stuff and ease your way home. We meandered the mile walk back to Union Station and split a breakfast at Beatrix, a little shopping at P.O.S.H., hit up our favorite Michigan Ave shops along the way: Anthropologie & LOFT, cocktails at Bottlefork, and lunch at Pearl Tavern, Champagne & Oyster Bar (don’t judge us, we were on vacation).

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We unfortunately never made it to Portillos or got our deep dish pizza, and we also stayed away from more of the true tourist Chicago must-do’s simply because we’d seen them before. Our budget wasn’t huge and we literally had 27 hours in the city before I had to catch my flight back to Minnesota, but we did a lot, ate some great food, caught up over some fun cocktails, and enjoyed the sights and sounds of the big city. I’ll be back Chicago!


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