Ok so I’m titling this post First Time In Chicago: The Perfect 3 Day Itinerary, but TECHNICALLY this isn’t my first time in Chicago. I visited about 10 years ago for work. But I was only there for 20 hours and literally only saw the airport, venue we were working in, the hotel (to sleep) and the airport again. So for all intents and purposes it was my first time in Chicago.
A friend of mine from college moved there a few years ago and I’m so so happy that I finally made it there. We had the most beautiful weather so I can’t recommend visiting in July enough. And 3 days in Chicago is the perfect amount of time to spend there.
I broke everything down by day so you could see our entire itinerary and everything we were able to do. But as with every city it’s pretty impossible to do and see everything. My friend, Mary, who lives in Chicago planned the whole trip. And honestly I wouldn’t have changed anything about our trip.
If you’re planning a trip to Chicago and have any questions feel free to email me and I’d be happy to help!
First Time In Chicago: The Perfect 3 Day Itinerary
So we were lucky enough to fly into Chicago’s O’Hare Airport late Thursday night and stayed the night at my friend’s apartment that we were visiting. So Day 1 we started bright and early and dropped our bags off at the ACME Hotel (more on that later). And headed right to the Skydeck for our 11:30 reservation.
We bought tickets ahead of time which I suggest if you’re going on a weekend or busy time of year. But you’re also at the mercy of the weather, which was, unfortunately, wasn’t on our side because we didn’t see anything but fog once we got to the top of the Skydeck at Willis Tower. It was still super cool, but if and when I go back to Chicago I’ll definitely do it again! Also the interactive experience leading up to The Ledge is awesome too. You learn a lot about the history of the city.
From there we took a cab to Millennium Park because whether you’re spending 1 day or 3 days in Chicago you MUST visit THE BEAN, or Cloud Gate if we’re being technically correct! You don’t need a lot of time there. But if you’re going to Chicago it’s a must-see!
Next, we walked down Michigan Ave onto the Chicago Riverwalk to find somewhere to have lunch!
All the restaurants along the Riverwalk are so cute with lots of outdoor seating and obviously amazing views. But we ended up at the Chicago Brewhouse! I always love to try local beers so I got the Half Acre Daisy Cutter, highly recommend! We were able to try lots of Chicago food favorites here – Maxwell Street Split Foot Long Chicago Style Hot Dog & Polish Sausage, Chicago Mini Italian Beef & Taylor Street Cold Cut Sub!
After lunch we were able to check into our rooms at the ACME Hotel and I can not even explain how in love I am with this hotel! It’s no surprise that they were named #1 Hotel in Chicago (and in the top 50 in the world) in Condé Nast Traveler’s 2019 Reader’s Choice Awards. And the #2 Hotel in Chicago in 2020! It’s super trendy, but also comfortable. Located right in downtown Chicago a few blocks from the river & the Magnificent Mile.
We stayed in King Suites which are perfect if you’re visiting with friends because it features a bedroom with a king size bed, a separate living room with a pull out couch, wet bar and desk and a spa inspired bathroom that is super Instagrammable!
After changing quickly we headed down to the Chicago River for the Wendella Boats Architecture Tour.
This was on the top of my list of things to do in Chicago. So I was really excited for it. My friend who lives in Chicago said it’s her favorite thing to do when people come to visit her too so I knew it was going to be great. She’s done the tour with a few different companies and Wendella was her favorite. I obviously have nothing to compare it to, but they were great.
The tour guide was entertaining and knowledgable. The boat was big and had a cover downstairs which was super beneficial towards the end of our trip because it started raining a little, and there was a bar! We did the Lake & River Architecture Tour specifically so our boat not only took us up and down the Chicago River, but then we went only Lake Michigan too!
After the boat we headed to dinner at 8:30 (highly recommend giving yourself a 30 minute buffer if you’re doing to dinner after the boat tour just in case the boat gets stuck in the lock coming back from the lake into the river.) Luckily we made reservations at a place not too far from where the boat let us off at Siena Tavern, a Modern Italian Restaurant.
Food was AMAZING and the overall vibe of the restaurant was exactly where we wanted to be on a Friday night!
Order a Dirty Martini with Blue Cheese Olives as your cocktail. For appetizers order – Coccoli (Crispy dough, stracchino cheese, prosciutto di parma, truffle honey) & Grilled Octopus (Crispy fingerling potatoes, red chiles, celery, aged balsamic). For entrees order – Truffle Mushroom Pizza (Roasted wild mushrooms, garlic cream, mozzarella, white truffle oil), Spaghetti (Jumbo lump crab, charred tomato, red chili & lemon cream sauce) and Gnocchi (Truffle cream, fried sage, crispy pancetta). End with an Espresso Martinis.
One of my favorite things about the ACME Hotel is that when you check in they ask you what time you’d like your morning coffee to be delivered to you! And every morning of your stay you’ll wake up to a thermos filled with coffee outside of your door! You can enjoy it in your room or take the thermos out with you to explore. Such a great touch!
We took our time getting ready that morning then took the train to explore Wrigleyville and Wrigley Field. The Cubs weren’t in town, but it was still fun to see the field and explore a different neighborhood of Chicago. Then we walked over to neighboring Boystown, one of the most country’s inclusive LGBTQ+ communities and the oldest officially recognized gay neighborhood in the United States, for Drag Brunch at the KitKat Lounge and Supper Club. Order the Bloody Mary (it comes in a martini glass) & Avocado Toast. And if you’re there for Drag Brunch and can’t score a seat inside, don’t worry they perform outside too!
After brunch we walked down to Replay Lakeview, this funky arcade themed bar for another drink then took the train back to the hotel to change.
Back to the hotel to change, headed to Rivers Restaurant for a wine tasting.
My friend Mary bought us all tickets to a wine tasting at Rivers Restaurant prior to dinner. The wine tasting was just ok. But we of course made the most of it and the restaurant itself was in a really cool location right on the Chicago River. But I can’t speak about the food because we didn’t try anything.
After the tasting we walked over to the West Loop for dinner at Cruz Blanca, a hip brewery and Mexican infused pub. The entire West Loop area was super trendy and seemed very cool. And while we didn’t get to explore it much if you have time definitely check it out. I didn’t actually realize it was a brewery when we were there or I would’ve tried the beer, what I can recommend is the Guacamole & the Crispy Shrimp Tacos (Gulf pink shrimp, epazote mayo, habanero pickled onions, roasted shishito chiles, arugula, lime)!
On our walk back to the hotel, we passed by the iconic Chicago Theater and obviously couldn’t resist snapping a few nighttime photos in front of it. Then Mary said it’s not your first time in Chicago without taking a shot a Malort, a Chicago tradition apparently, and while it was absolutely the most vile thing ever, if it’s a Chicago tradition I was all for doing it. If you want to I highly recommend looking for a local dive bar to order it in!
We had reservations at The Berkshire Room, the trendy cocktail bar located in the lobby of our hotel that night so we headed there after and it didn’t disappoint! We toasted with Snack-quiris (mini daiquiris to start and I have the Careless Whisper (Sparkling Rosé, Bermamot, Amontillado Sherry, Lemon & Strawberry).
After enjoying coffee in our room again, we got up and took one last walk down to the Riverwalk because it was such a beautiful morning, then we checked out of the hotel.
We headed over to ERIS Brewery & Cider House in the Old Irving Park Neighborhood of Chicago for brunch. If you’re there for brunch order the “Choose Your Own Adventure” Bloody Mary with a Sidecar of ERIS Beer. Then I highly recommend the Cheese Curds (Wisconsin cheddar, rice flour tempura, chipotle ranch and maple mustard for dipping), Waffles of Chaos (Belgian Liège waffles, applewood bacon, avocado, radish, cheddar/jack cheese, sunny-side up egg and Sriracha maple syrup), Chilaquiles (Homemade tortilla chips served warm in chipotle-tomatillo salsa, with avocado, pickled jalapenos & onions, vegan sour cream), Chef’s Burger (Half pound patty, parsley-scallion pesto, arugula, marinated tomatoes, goat cheese, caramelized red onions, honey drizzle, toasted polenta bun) and Crispy Cauliflower Wrap (Crispy smoked cauliflower, garlic buffalo sauce, arugula, tomatoes, pickled onions, scallions, vegan cheddar, garlic aioli, flour tortilla).
After brunch we headed to Kathy Osterman Beach because it was the most perfect day and we couldn’t visit Chicago in the summer without take a dip Lake Michigan. As someone who grew up on the East Coast and going to ocean beaches, I was in awe at how huge Lake Michigan was.
Then we headed back to Mary’s apartment for the finale of our Chicago trip – CHICAGO DEEP DISH PIZZA!
We got Mary’s favorite Pequod’s Pizza and it did not disappoint! If there’s one thing you have to eat in Chicago it’s deep dish pizza and while I only got to taste one kind I really can’t imagine you being disappointed in anyone that you try!
The next morning we packed up and headed back east after a perfect 3 days in Chicago.
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