72 Hours in Chicago


I had the opportunity to make a quick weekend trip to Chicago to visit friends from Montana last summer. These ladies are my FAV people to travel with because they are all so laid-back, easy-going, and generally positive wonderful people. I forget what an amazing city Chicago is and I feel like I need to make an apology? Like you're still in the midwest (convenient for those of us in Minnesota), but it's like you're on a (very cold) beach because of Lake Michigan, and it's a huge glamorous city with limitless amazing places to eat and drink and be merry. Seriously, if I lived there I don't think I could ever eat at the same place twice, there were too many amazing restaurants. I left about thirty minutes after my last final for a six hour drive which, in hindsight, was more stressful than I thought it would be, BUT overall an amazing weekend and I have so many things to recommend. :-) 



So technically I stayed with a friend, who's amazing apartment had 360 degree views of downtown Chicago and Lake Michigan (shoutout Grace). However, Chicago has an AWESOME burgeoning boutique hotel scene that needs to be acknowledged. 

1. Hotel Lincoln

We visited a friend in the coffee shop at this adorable boutique hotel, and I maybe fell in love... with the hotel, to clarify. The location couldn't be better, away from the constant crowding of the mag mile, but still near the action with amazing views of Lake Michigan (literally across the street) and Chicago's incredible skyline. Not only do they have a great coffee shop with a killer lavender latte, but they're pet friendly, have free bike rentals, rooms starting from $109, amazing amenities, designer rooms, The Kennison - one of Chicago's best eateries, a trendy rooftop bar... should I keep going?!? Did I mention they're pet friendly?! 

2. The Guesthouse Hotel

If you're ballin' without a budget, checkout this somehow boujee-but-understated stay. It's classy as hell, and they seriously make every effort to make you feel at home, starting with an email before you even get there containing tips about how to best enjoy Chicago. The lobby is beautiful, if you really want to impress you can even hold an afternoon tea for you and your guests, and every suite contains a beautiful, light-filled kitchen. Decadence comes with a price, though, and you can expect to splurge for this hotel. 

3. The Ivy

If you're more of an urbanite who wants to be near the action, the Ivy is for you. Located in River North, steps from mag mile, this hotel is near all the action you could ask for. It's a very small, very new boutique hotel with all kinds of techie amenities, clean white backdrops, rainfall showers and soaking tubs, and located right next to Navy Pier and Lake Michigan's shoreline. The price point is super affordable, with their most luxurious room, a King suite, starting as low as $152. 

4. Soho House

Okay you guys this hotel/member's club is built exclusively of dreams, I am almost positive. It's a little on the pricy side, with small 200-300 sq ft rooms starting at $170-200, but for all the unique amenities included that seems like nothing. They have a 17,000 sq ft gym with a professional boxing ring and technogym equipment. If you're, say, holding a private screening, they happen to have a private screening room with red velvet arm chairs. A contemporary art collection, a 60 foot long rooftop swimming pool and terrace, and a service feature called "One While Changing" where bartenders travel room to room with bar carts to mix you a drink while you get ready for the evening. RUFKM. Made of dreams. 



I'm going to do a separate category for both eating and drinking here, because the bar scene and food scene were both too incredible to not pay separate homage to. 

1. The Hampton Social

Possibly the most instagrammable brunch spot EVER. Whoever decorated this restaurant's interior, if you're reading this, please contact me asap. Anyone who knows me knows I have an unhealthy obsession with both brunch and rosé, and this restaurant delivers on both. Big time. They have an awesome nautical theme inside, paired with a giant neon Rosé All Day sign that I would have stolen if I knew how (just kidding. kind of.) and amazing food and drinks. We went on a weekday morning and it was easy to get a table, plus they kindly obliged our annoying request to sit in the more photogenic part of the restaurant. Life of a blogger, what can ya do. 

Order the Butternut Squash Toast (a surprisingly wonderful twist on Avo Toast) and the Frosé All Day

2. Beatrix

Guys, this place is so good. There are three locations, so you'll probably be within walking distance (or a short Lyft ride away) from one of them at any given time. SO many good things. First of all, they have drinks made with fresh-squeezed juice and things like charcoal and turmeric, so you can detox while you retox. Multi-tasking at its finest, ladies and gentleman. Second, I had very possibly the best veggie burger of my life there. A mushroom and quinoa burger with Sriracha aioli. I think I could eat it for every meal, for the rest of my life, and not complain. They all kinds of vegetarian and vegan options. 

Order the Mushroom & Quinoa burger and the Black Cherry Sangria

3. Lula Cafe

Farm-to-table, a neighborhood staple (rhyming unintentional), AND a six course vegetarian tasting menu. What. This quirky cafe was sourcing locally before it was cool, and their veggie-loving menu makes it super easy for vegetarians and vegans to find all the dishes their hearts could desire. A tasting menu?! I'm not over it. They also have an incredible brunch that consistently creates a line out the door, with dishes like Brioche French Toast with cardamom anglaise and Gnocchi Alla Romana (you know I have a soft spot in my heart for gnocchi). Go for lunch, brunch, dinner, or anywhere in between and you won't be disappointed. 

Order the vegetarian tasting menu with wine pairings

4. Marisol

Marisol is the kind of ultra-trendy restaurant where you wonder if everyone thinks the menu looks like it was printed in twelve foreign languages put together, or it's just you? I'm not kidding, I understood maybe half of every menu item. This restaurant is located in the MCA and is immersed in art everywhere you look. Even though the menu may look intimidating, the food is truly amazing. Order family style and pass out around a multitude of dishes to really experience the impressiveness of the food here. My favorite was the Celery Root Involtini, and I'm still not entirely sure what that means but it has to do with celery root pasta. Close your eyes and point at a menu item and you're pretty much guaranteed to enjoy it. 

Order the Burrata and the #13 cocktail to start

5. Hot Chocolate

With a name like Hot Chocolate, you might think that the menu is limited to, say, hot chocolate. But this restaurant is multi-faceted - not only do they indeed have amazing hot chocolate - eleven different ones, to be exact - they also have incredible dinner and brunch menus. This restaurant is soo cozy and located in a very homey neighborhood we walked around in for hours, with all kinds of unique little shops. 

Order the Market Grain Bowl and the Affogato (Dark chocolate hot cocoa with coffee cocoa nib ice cream)



If you want to spend your night drinking $14 cocktails in a high end bar, I'm your girl. Does my bank account send out a silent plea for help every time I go out? You bet. As anyone in college, I can appreciate a good dive bar every now and then, but through and through I am someone who loves a beautiful bar. Chicago has an amazing scene for craft cocktails, and I only barely scratched the surface. Here are my top three. 

1. Three Dots and a Dash

What's better than an unmarked bar you have to know about to find? An unmarked bar that also happens to be a Polynesian paradise and one of the top 50 bars in America. Enter a nondescript side door in an alleyway and transport yourself to the next best substitute for an island vacation. The drinks are nearly as beautiful as the decor, served in giant clam shells, treasure chests, and coconuts with dry ice for added emphasis. Make a reservation if you don't want to wait in line for hours. 

2. Disco

"Disco re-creates the energy, glamour, sexiness, and globally-fueled character of the 1970s from Paris, Rome, and NYC." Say no more. This is the upper level of a multi-floor restaurant called Celeste. Also, the entire floor lights up. Words cannot do it justice. I was there after 1 am and my memory is slightly hazy (sorry mom) but even still I was so impressed I will forever recommend this bar to anyone visiting Chicago. Also - they're open until 4 am, which is such a pleasant change from the 2 am bar-close nonsense of the US. 

3. The Violet Hour

I seriously have a thing for unmarked bars. If you can call it that, because a large mural and single light bulb let you know you've arrived. If you want to pay homage to Chicago's cocktail renaissance, this is the place to go, having been attributed to inspiring it. I love the house rules, which include, but are not limited to, no cell phone use, proper dress code, "no o-bombs, no jager-bombs, no bombs of any kind".



After all of your eating and drinking and recovery from the eating and drinking, if you still find time to go out and do other things, I commend you. Here are a few ideas. 

1. Magnificent Mile

So. Many. Stores. Whether you're looking for Chanel luxury or Forever 21 affordability, you'll find a store for it on the magnificent mile. Basically a huge outdoor mall, but better. 

2. Skydeck

I always try to throw in some locations that will benefit both your trip and your Instagram grid, because let's face it we're all trying to get a few good IG posts out of our travels, no shame there. You can go to the 103rd floor and climb out onto the clear observation deck, sweaty palms and all, to look 103 floors below your feet to the street. And get your pic for social media. 

3. The Second City or The IO Theater

I'd never been to improv show and I went to two at IO while in Chicago and loved it! Second City is a bit more well known, having hosted many comedy stars, but both are great places to catch a show. Tickets range from $5-40 but are relatively affordable, especially at IO. 

4. Millenium Park

Again, do it for the gram. Though this park gets pretty tourist-y... it has the bean. The great silver bean. 

5. Navy Pier

Inside the Navy Pier it gets real tourist-y. Think Jersey-Shore-esque t-shirt shops. But the Ferris wheel is beautiful and so is Lake Michigan, even in the winter cold. There are also winter attractions like ice-skating inside. 

6. Lakefront Trail

Again, let me reference the beauty of Lake Michigan. Basically like taking a very cold walk along the ocean. But it's a lake, so it's cooler (no pun intended). Spanning 18 miles, there are plenty of beautiful skylines and gardens to encounter. Just make sure you bundle up. 

7. Wicker Park

An awesome trendy, but not too trendy, little neighborhood. We took the L here to visit many a coffee shop and secondhand store. As well as not-so-secondhand stores like Free People, Urban Outfitters, and the like. Stan's Donuts is right off the subway and you don't want to miss your opportunity to stop here. SO. GOOD. We also made a quick stop at En Hakkore 2.0, which is much more aesthetically pleasing than it looks outside, and I ate the best (and... well, first) sushi burrito I've ever had in my life. 

Sedona Anderson8 Comments