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Chicago in 48 Hours: Chicago’s Best Restaurants, Sightseeing, and Friends

Recently, one of my best friends and former roommates, Tiffany, moved to Chicago to further her education in medical illustration. Our other best friend from high school, Karla, and I promised Tiff that we’d visit her and explore her new city – if you ever make that kind of promise to a friend, you are out of your mind if you don’t find a way to make it happen. A couple of weeks ago, Karla and I hopped on a quick flight from the Atlanta airport to Midway, where we met Tiffany and hit the ground running on our whirlwind tour of Chicago.

In 48 hours, we saw the city from corner to corner. More importantly, we ate our way through Chi-town, having monumentally delicious meals for breakfast, lunch, and dinner. Since our trip revolved around the cuisine, so will this blog post.

DAY 1: 

Lunch – Giordano’s Pizza

What’s the first thing you have to get when you arrive in Chicago? Chicago-style deep-dish pizza. Duh. We enjoyed our individual “baby” pizzas (this is a misnomer – deep dish pizzas are pretty filling, even if they are baby-size) before heading to Millennium Park, where my most sought-after attraction awaited: The Bean!! I’ve been bothering Tiffany for weeks about how I was just dying to visit the landmark, it lived up to its expectation:

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After checking out all of the statues and strange artwork, we continued toward a spot high on everyone’s list: the Magnificent Mile for shopping!

Dinner – American Junkie

This place is amazing. Great atmosphere full of young, hip Chicago-ites (Chicagans? Chicag-ians?) and gourmet food for great prices. Karla enjoyed a BBQ chicken flatbread and I got the shrimp and mushroom risotto…but Tiff’s pork belly sliders were the prettiest:

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Everything was over the top delicious, a perfect meal to kick off our first night in town. After dinner, we walked to Navy Pier, where, without hesitation, we hopped in line for the Ferris Wheel.

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As touristy as this is – DO IT! We timed our ride perfectly for beautiful views of the skyline at sunset. This was the exact moment I fell in love with Chicago.

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Our night wouldn’t have been complete without cocktails and dessert at the Signature Room, located on the 95th floor of the Hancock Tower. We lucked up with one of the mot amazing views – it’s like Chicago knew we were celebrating three belated birthdays and about ten years of friendship. Hats off to you, Chicago, for the warm welcome.


Day 2:

Breakfast – Glazed & Confused

This morning, we set out on a mission…and that mission included donuts. When we discovered the line for the Donut Vault was out the door, we remembered a coffee shop we passed on the way with fresh pastries in the window. So, we backtracked, checked out the homemade donuts, courtesy of Glazed & Confused, and selected a toffee, maple bacon, and creme brulée. We could not decide which one was our favorite.

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Naturally, we had to do some walking to make up for the donuts (can I just talk about how we walked approximately 30 miles in 48 hours in flip flops? Go ahead, tell us how incredible we are. We know.), so we trekked back to Navy Pier to go on an architectural boat tour of the city.

Despite the horrible sunburns we all received (we’re each sporting some variation of farmer’s tan), this tour was absolutely worth the money (only $32 per person!). I’d highly recommend taking it – I never knew how to appreciate architecture before hearing all about it. Now, I can say that I like a building that is more modern and, instead of simply calling a building ugly, I’ll know that really, it’s just a form of brutalism. So I’ll start calling ugly buildings brutal.

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Since we got such a late start with our breakfast, we wound up skipping lunch completely. Instead, we kept exploring, grabbing a cab over to the aquarium, thinking that no one would be at the Chicago aquarium in the middle of a Friday. Wrong. The line wrapped around the building into the heat of the midwest sun.

We skipped the aquarium and decided to walk around through Grant Park, onward to the Buckingham Fountain, which were all just beautiful. The number of sights in Chicago is just astounding – it’s a really pretty city, I fell more and more in love with it each day.

Dinner – RPM

Per Tiffany’s suggestion, we had to try one of her favorite Chicago restaurants, RPM. Having lived with Tiffany most of my semi-adult life, I trust her taste in food (except when she once prepared her own sushi in our college apartment kitchen. I can’t handle that) and, more specifically, I trust her taste in desserts. Tiff can whip up the best homemade desserts you’ll ever taste, especially her Chocolate Chip Cookie Dough Cupcakes.  If she wasn’t already in school for medical illustration, I’d say she should go to culinary school and I would be her bakery’s first customer.

Tiff had previously tried RPM’s Tartufo dessert, which is essentially a giant version of a Ferrero Rocher chocolate. This just so happens to be one of my favorite types of chocolate (granted, every type of chocolate is my favorite type of chocolate). The dinner – I had the Truffled Gnocchi – and dessert at RPM did not disappoint.

After dinner, we rushed home to Tiffany’s apartment for the ultimate girl’s night in (plus, it was storming). I will not tell you all that that involved, but be warned that Channing Tatum and sangria made their appearances.

DAY 3:

Brunch: Batter & Berries

Any place that serves French Toast Flights is going to have my attention – this made Batter & Berries the perfect brunch spot on our way to the Lincoln Park Zoo. Their French Toast doesn’t just have strawberries or blueberries on top of it – no, this place dips each piece of French Toast into various flavored batters. My flight included strawberry, blueberry, caramel, and lemon (the latter being my favorite) and we all shared the special of the day: Oreo French Toast.

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We were happy campers on our last morning in town, eating just enough to walk it off on a quick trip to Lincoln Park Zoo, an attraction so nice I still can’t believe it’s completely free. Tiffany has periodically sent us photos from the zoo over her past year in Chicago, so it was a fun way to end an incredible 48 hours in the city.

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Next time you’re in Chicago, be sure to try some of these delicious restaurants, and don’t forget to ask me about our fabulous partner properties in the area where I can get you extra perks: The Ritz-Carlton, A Four Seasons Hotel (there’s a story behind that one – it’s actually a Four Seasons and no, it isn’t having an identity crisis), the Peninsula, Trump Towers, Park Hyatt, and the Sofitel.

Lindsey Epperly

My name is Lindsey Epperly and I’m a travel consultant and owner of Epperly Travel, a national affiliate of Century Travel. I’m most passionate about building lifelong relationships with my clients and suppliers, discovering the globe in a way that makes me a better agent, and celebrating with my team when we reach a new milestone. One of our core values at Epperly Travel is to create fun and celebrate constantly – and I’m fortunate to be in a career that allows me to do just that. I’m proud to announce my recent achievements: landing a spot on Wendy Perrin’s WOW List as their Caribbean expert, being nominated for Virtuoso’s Rising Star Award and receiving a place on Jezebel Magazine’s Trailblazing Ten list.

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