Chicago, Illinois has been at the top of my U.S. travel bucket list for years. Not just because I’ve always heard it’s one of the coolest cities in the Midwest (which it totally is), but because I was born there. It’s right there on my birth certificate — but since my family left for Los Angeles before I was even able to form words it’s not like I know the Windy City. Not in the least.
With a curiosity about where I came from brewing, I finally packed my bags for the Chi (do non-residents who were born in the city get to call it that?) after 25 years away. I only had three days to explore Chicago’s famous food spots, nightlife scene, and classic tourist attractions, so I wasted no time lounging around. A few early thoughts before we get more granular:
- If you’re Ubering everywhere, you’d better budget for it. I didn’t and had to walk nine miles in the heat one afternoon to get from place to place while saving cash.
- The Windy City lives up to its nickname. I brought a flowy skirt and may have flashed a few locals on accident.
- While the high temperatures and humidity are no joke in Chi-Town, summer is undoubtedly the best time of year to visit. From bikers zooming down the 18-mile long Lakefront Trail to young partiers chilling out at North Avenue Beach, Chicago’s lively summer vibes are perfect for adventure and party-friendly 20-somethings.
Below, you’ll find the mix of mainstream tourist attractions and low-key deeper dives that filled my days and nights. Of course, deep-dish pizza was a must on the to-do list but it was the trendy rooftop bars, authentic Greek cuisine, and a crystalline skyline that made Chicago one of the most memorable U.S. trips of my 20s, thus far. Check my full recommendations below:
PART I – Where to Get the Best Views
360 Views at The Signature Lounge
There’s no shortage of sky-high window views in Chicago, but one (literally) stands above the rest. The Signature Lounge at 96th is a bar and restaurant (The Signature Room at 95th) at the top of the iconic John Hancock Center. The lounge’s upscale ambiance and dress code make it a splurge-worthy destination for starting a celebratory weekend out on the town. To get here, you first wait in line to take an elevator that somehow races up 96 floors in less than a minute.
Be prepared for slight vertigo and roller coaster-like G-force if you’re sensitive to motion. Fear not, the view is worth the 30 seconds of discomfort.
The elevator doors open to floor-to-ceiling glass walls that offer a bird’s eye view of where the concrete jungle meets the icy blue water of Lake Michigan. Take a lap around the lounge and you’ll observe couples dressed to the nines for a date night, tourists snapping pictures of the awe-inspiring landscape (yes, I was one of them), and perfectly groomed waiters running glasses of specialty cocktails and champagne to their tables. On the far side of the lounge, you’re met with a sea of skyline that drifts into flat Midwestern terrain disappearing into the horizon.
If you can, go to The Signature Lounge at 96th during sunset. I’m not exaggerating when I say it took my breath away, but I’m also a sucker for a good sunset view.
Want to experience the spectacle for yourself? View the full menu and photo gallery here.
The J. Parker Rooftop at Hotel Lincoln
I booked a room at Hotel Lincoln for the weekend, which happened to be home to a popular brunch and nightlife rooftop called The J. Parker. This rooftop reminded me of a classic Saturday afternoon back home in LA. There were groups of young people, all dressed like a photo straight off Instagram’s Explore page, crowding the hotel lobby anxiously waiting in line to get the signature cocktails flowing. I ordered the “Bubble Around,” a tantalizing concoction made of vodka, lemongrass, elderflower, lemon, and prosecco.
The best part of The J. Parker was the unobstructed view of Lake Michigan and Lincoln Park. You can admire the lush greenery of the park at lunch, peer out at sailboats cruising by at sunset, or take in the city lights while you sip after dark.
Pro tip: If you book a stay at Hotel Lincoln, you get to jump the line for a table. The wait time for The J. Parker can get up to well over an hour, so it’s worth considering getting a room. Not only that, but the hotel is in the heart of the Lincoln Park neighborhood that’s only a short walk to Old Town, North Avenue Beach, and Lincoln Park Zoo.
Click here to book a room at Hotel Lincoln.
PART II – Where to Party
The Old Town Bar Scene
Looking to get lost in the night? Head to Wells Street in Chicago’s Old Town district. Walking distance from Lincoln Park, Old Town is filled with a plethora of bars, restaurants, and boutique shops. After dark, this historic stretch becomes a party scene where hundreds of young people scatter (or should I say stumble) from bar to bar. It reminded me of an elevated version of my university’s main street – bordering on chaotic but in the best way possible.
On one side of the street, there’re flashing lights and techno blaring at Benchmark. On the other side? A chill Irish sports pub where you can grab an authentic Irish beer to kick off the night. Just steps from the pub is a late-night pizza spot called Happy Camper complete with a disco ball, refurbished trailers, and a beer garden-esque atmosphere.
There’s truly something for every kind of gen-Z and millennial bar hopper in Old Town. My personal favorite Old Town hotspot was Happy Camper simply because of its quirky decor and cocktails.
Here is the full Happy Camper menu.
The Second City Comedy Club
Chicago’s Old Town is also home to where some of the greatest comedians, award-winning actors, and directors of our time got their big break. AKA, The Second City. It’s a comedy club and school where you can go to get some belly laughs and drinks on a night out. Notable names you might recognize (and by “might” I mean “definitely know and love”) include Bill Murray, Chevy Chase, Gilda Radner, Aidy Bryant, Cecily Strong, Mike Myers, Chris Farley, Key & Peele, John Belushi, Jane Lynch, Tina Fey, and Steve Carell…just to name a few.
If you want to understand the arts of improv and sketch comedy, this is a must-visit destination.
Click here for The Second City’s latest show dates, news, and classes.
PART III – Where to Eat
Chicago Pizza and Oven Grinder Co.
I didn’t know I could fall in love with a meal until I went to Chicago Pizza and Oven Grinder Co. This little wooden restaurant is comprised of a refurbished house that lies directly across the street from the scene of the infamous Saint Valentine’s Day Massacre in 1929. It’s even rumored to have been the lookout post for henchmen of the Valentine gunners.
One step into the foyer and your nostrils are met with a steamy combination of garlic, marinara, and warm dough. But this isn’t any old pizza place. It’s a pizza pot pie place. The individual serving-sized pies are made from scratch with triple-raised Sicilian bread, a homemade sauce, and a blend of cheeses that made the post-dairy stomach ache worth every. Single. Bite.
If you can’t wait for your pizza pot pie to bake (no shame, I couldn’t either), order the Mediterranean bread as an appetizer for the table. This massive, herby pull-apart flatbread reminded me once again why I’ll never go on the Keto diet.
Tables fill up fast, so you’re going to want to make a reservation here.
Authentic Cuisine in Greektown
A bit off the beaten path and less congested with tourists is Greektown. What was once a Greek immigrant community is now a commercial district. However, the cultural influences of the past still remain, as you’ll see passing by the many Greek restaurants, tavernas, and pastry shops. The restaurants, of course, are always my favorite part.
You know the feeling of being so satisfyingly full after Thanksgiving dinner that you can barely move? That’s exactly how I felt after leaving Greek Islands, a restaurant in the heart of Greektown that’s been filling its tables since 1971. The restaurant imports its extra virgin olive oil, wine, cheeses, seafood, olives, herbs, and spices directly from Greece, so you know you’re getting the real deal. The sampling of hummus and Taramosalata on my plate teleported me to the hillsides of Santorini. The traditional blue and white decor helped, too.
Out of everything on the menu, it was the flaming saganaki cheese that did it for me. I didn’t know whether to be scared or excited when the block of cheese burst into an orange flurry right next to my table. It was like a culinary circus act and I was the dancing bear waiting for my treat.
Ready to try the flaming cheese for yourself? View the full Greek Islands menu here.
PART IV – Where to Sightsee
Architecture River Tours
Chicago is often referred to as the “Second City” because it was rebuilt from the ground up after the Chicago Fire of 1871 left much of the city in ashes and one-third of the population homeless. What replaced the damage is a slew of skyscrapers highly recognized for their impeccably executed and creative designs. To get a closer look at the legendary structures and learn more about the city’s history, take an Architecture Boat Tour on the Chicago River. It’s maybe the most efficient and affordable way to experience most of the city without sacrificing too much of your party or dining time.
Your tour guide takes you on a 90-minute cruise that gives you in-depth detail about the tallest, oldest, and most gravity-defying buildings in Chicago. My neck was hurting by the end of it because I didn’t want to miss a single landmark.
If architecture doesn’t pique your interest, Chicago Line Cruises also offers a variety of other cruises, such as a historical tour and a live jazz tour.
Click here for the full list of options.
Historic Navy Pier
One of the most animated destinations during summer is Navy Pier. Here, you’ll find a 200-feet-tall Ferris wheel, classic carnival games, lakeside dining, sporting event watch parties, art installations, and even live performances from local dance groups and theater organizations (just to name a few). I even saw a wedding party boarding a yacht off the side of the pier for their reception.
Every Wednesday and Saturday night during summer, the pier also puts on live music and fireworks. Make sure you get to a rooftop bar or nearby park by 9:30 p.m. if you want to catch the show. If you go to the pier midday, wear sunscreen or a hat. The crowds of people and light reflecting off the water will heat you up in a hurry. I could almost hear the skin on my shoulders sizzling by the time I left.
Follow the link here for Navy Pier’s complete schedule of public events and programs.
The Bean at Millenium Park
I couldn’t go to Chicago without making a stop at “the bean.” Possibly the most Instagrammed piece of artwork in the Midwest, Cloud Gate (more popularly known as “the bean”) by Sir Anish Kapoor, can be found at the Chicago AT&T Plaza at Millennium Park. Unfortunately, it was gated off to abide by social distancing guidelines at the time of my visit. So I didn’t get the classic bean selfie in the mirrored surface of the sculpture. The upside is that I was able to take in the full essence of the piece, catching every glimpse of the skyline reflected against it.
As majestic as it was, I couldn’t help but think of a giant, silver Flubber. The surrounding area in the plaza is made up of walkways, futuristic architecture, and a queue of trees that offers a much-needed escape from the heat.
Curious to learn more? Here is the full rundown about the bean’s history, design, and location.
It’s safe to say that Chicago did not disappoint and there’s still so much to do and see (the jazz clubs! the theater scene! the avant-garde art!). A weekend doesn’t give you enough time to soak in everything the city has to offer. Will I be moving back? Not until I witness one of those famous Chicago winters. But I definitely won’t go another 25 years before returning to my birth city — that’s for sure.