48 Hours in Chicago

I’ve always thought of Chicago as a smaller, cleaner version of New York with some midwest flavor sprinkled on top (but not so much that it loses it’s edge). Growing up in Minnesota, we made the drive to the windy city several times, but over time my attention shifted to other cities that were trendier and new to me. I had forgotten how much I love the history and landscape of Chicago, until a few weeks ago when I landed in O’Hare for a quick two day work trip.

If you happen to go in the dead of winter like I did, I HIGHLY recommend you bring more than a trenchcoat.

Just like my Portland trip, if I’m visiting a city on my employer’s dime, I’m definitely going to pack every second of my off time with some exploration (what is it about something being free that makes it that much more fun?). I’m sharing a full breakdown of everything I saw & did while there! My two days were full of art, ghost hunting, great food and champagne. Enjoy!

The Hotel

I stayed both nights in The Hotel Lincoln in the Lincoln Park area, and it was hands down the best hotel experience i’ve ever had (not sponsored). They texted my work phone the day before check in, asking if I had any special needs/requests and if I was celebrating something special. I let them know I was celebrating a promotion (maybe true, maybe not), so they had wine, chocolate, and a handwritten card waiting for me when I got there!

They called my room halfway through the trip to make sure I had everything I needed, and gave me some great advice on where to spend extra time. This is why I make a habit to seek out boutique hotels these days, whenever possible. The service really made a difference, and the room itself was spacious & comfortable.

This neighborhood is definitely nice and I felt comfortable/safe walking around alone. It’s right around the corner from Old Town, which I didn’t explore but apparently is full of restaurants and shops. It is also a short uber ride away from anything downtown you’d want to see.

No complaints!

Night One

There wasn’t much time after I got settled in, so I grabbed a drink and bite to eat at the hotel’s rooftop bar: J. Parker. They make a mean dirty martini, but the real draw here is the view and (in the summer) outdoor space. This isn’t a great place to go if you’re trying to mingle and make conversation with a stranger or two, at least not on a weeknight. But if you’re tired and want to relax in style, J. Parker is perfect.

Day One

My morning started off with a quick work breakfast at Nookies not far away in Lincoln Park. This place feels like it came right off the set of Gilmore Girls. It’s no-frills as far as the interior goes, but it is clean and the service is wonderful. The tagline on their website is “Fresh and Friendly since 1973.”  Halfway during our yogurt parfaits, I heard the *pop* for a Champagne bottle a few tables down. Confusing, since there’s no alcohol on the menu and I would never assume a little cafe like this to serve cocktails. I started looking around and, lo and behold, a table of girls were on their second bottle of champs & two guys next to them were splitting a 6 pack over their omelets. This place encourages you to BYOB! Note to self for next time! Imagine how much money you’d save on brunch if more places allowed for this?!

From Nookies, I went straight to my lunch meeting at Crosby’s Kitchen in the Lake View neighborhood, where I ordered the veggie burger (very good!) and my guest had the crab cake sandwich, which he apparently loved too. The place was packed during the lunch hour, so I recommend making a reservation. Great service here, too! It’s in a great location on Southport Avenue within walking distance to tons of shops and places to wander into. I especially liked the US Apothecary shop that’s one or two doors down from Crosby’s.

The real MVP of this whole trip was my evening at the Congress Plaza Hotel, AKA the most haunted hotel in Chicago. Quick background: The hotel was built in 1893 in the South Loop for the crowds of visitors in town for the World’s Fair (how could there not be major stories there?), and remnants of its regal history can be felt throughout the whole place to this day since parts of it are relatively untouched. Within minutes of sitting down at the lobby lounge, the bartender had already been hooked into spilling the dark history of the place, along with his own personal stories. He’ll tell you that the most haunted floors are 4, 6 and 12, and that Al Capone had run his whole operation out of the 10th floor throughout the 1920’s and 1930’s (makeshift brothels and booze transport through tunnels to his nightclub across town during the prohibition era… nothing major).

The ghost(s) of the 12th floor are my favorite. During WWI and WWII, the hotel housed refugees from other countries, 3 of which were are mother and her two young sons (from either Prague, or Poland) as they waited for their father to join them. There are differing accounts, but one day the mother either gave up on his return/learned he was dead/thought they would be deported and completely lost her shit. She reacted by throwing her two sons out of a 12th story window, and then herself. One or both of the boys have been seen regularly roaming the halls.

You can bet I took it upon myself to explore each floor. I may have found an open door and gotten a closer look at one of the newly remodeled rooms. ALLEGEDLY.

This hotel even inspired a Stephen King novel – 1408. If you aren’t sold on the fact that this place is worth at least a visit, I give up! (Below is a photo of me on the way to the 12th floor, actually preparing to meet my fate.)

Want more stories? Check this out. This other list references room 441 as the most haunted room, which our bartender echoed. But when I walked the length of that floor multiple times, I could not find that room. I swear it doesn’t exist.

Day Two

The coffee shop attached to The Hotel Lincoln lobby, Elaine’s Coffee Call, serves great drinks made with handmade syrups and a nice atmosphere if you need a place to work for a few hours. I grabbed an almond latte there on Saturday morning and then headed to the Museum of Contemporary Art. It’s $12 a ticket for a solid 1.5 – 2 hours (possibly more if you want to join in on a guided tour) of enjoyment for someone who has no background and very little knowledge of fine/modern art.

From there, I wandered down to Michigan Avenue, because it was close by and at my core I am still a cheesy tourist. After fulfilling a childhood dream of visiting the American Girl Store at Water Tower Place, I booked it to The Ralph Lauren flagship/largest store down the street. Walking through those doors was like coming home, not because I feel a particular allegiance to the fashion mothership for WASPs everywhere, but because there were fancy servers walking around offering trays of champagne and cocktails for shoppers. This place is decorated like a wonderful multi-story home owned by Jay Gatsby/a pro-golfer/your martini-allegiant grandmother.

But the store itself isn’t all there is. Walk to the back of the store and you’ll see a semi-conspicuous door with no obvious signage. That door leads to the Ralph Lauren restaurant. This place is so charmingly bougie it’s hard to hate. If you’re stopping here for a drink or bite to eat, you need to know you’re going to need either patience or a reservation, and you had better be wearing a good outfit. While you wait, sit at the bar and admire the decor and a fancy cocktail. The atmosphere and decor here is a seamless extension of the RL store, which is exactly why people love it.

There you have it! Are any of you from Chicago, or have recommendations? I’m hoping to plan a trip back there this summer with a few friends and would love your input! Share in the comments?



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