Chicago is such an easy weekend trip from Louisville and I love every time I make a visit! I’ve recently gone for a work trip and to celebrate a friend’s birthday, so I wanted to combine the two into a general weekend guide for the Windy City! There’s obviously so much to do in this large city, but the below gives you a variety of activities to choose from.
My biggest recommendation is to book your reservations early! Chicago is a busy city, and the popular restaurants fill up well in advance.
Friday / Day 1
Upon arrival, check into your hotel or Airbnb, and have some snacks and drinks while you get ready for the evening. Start off the weekend right with dinner at delicious Italian dinner at Alla Vita or Topo Gigio. While these are two totally different vibes, they’re both delicious Italian spots with food that is sure to get your trip started off right. They are also both located in neighborhoods with plenty of bars to visit afterwards if you’re not too full from dinner.
Alla Vita – located in the popular West Loop and with trendy vibes galore, this place is a five star spot. From the cocktails to the entrees to the gelato desserts, you will absolutely not be disappointed.
Topo Gigio – a more authentic and classic Italian spot in Old Town, the food and service are top notch and their espresso martinis and dirty martinis make it impossible to have only one. You’ll need to call to make a resi here!
Day 2 / Saturday
If you’re up for activity, there are plenty of paths to walk or jog along which is one of the reasons I love Chicago! Check out the Lakefront Trail, and hop on/off wherever you’d like.
Start your day with an incredible brunch at Pizzeria Portofino, and be sure to try your damndest to sit outside! I honestly felt like I was in a different country looking at the water and sipping on a limoncello spritz. Bonus if it’s a beautiful day like it was for us… truly I could’ve sat there for hours. And the pizza is… chef’s kiss.
If you can tear yourself away, walk along the river to work off some of those carbs. Stop and have a drink at Tiny Tapp on the water, a perfect daytime spot to watch the people and boats.
Depending on what you’re up for during your day, there are a variety of things to do:
Skydeck Chicago – stand on the ledge of the Willis Tower and overlook the city. Tickets are pretty affordable at about $36/adult.
Wendella Boat Tour – learn about Chicago architecture while you cruise down the Chicago River. This is truly such a cool experience and even better if it’s a beautiful day. Tickets range between $28 – $44/adult pending which tour you book. Cocktails and beer/wine available for purchase on board.
Lincoln Park Zoo – this is a FREE experience and I’ve heard it’s one of the better zoos.
Shop along Magnificent Mile – Chicago’s Magnificent Mile is known for it’s shops! Cruise down the street and pop into all your favorite spots.
Now that you’ve worked up an appetite, it’s time for another mouth-watering Chicago meal!
Aba – one of the best restaurants I’ve been to, for both the ambience and the food. I am a sucker for Mediterranean cuisine and this takes it to the next level. Recommendations: short rib hummus, charred eggplant spread, grilled salmon kebabs.
Mercadito – delicious margaritas and coastal vibes, a really fun spot for a smaller group. The serving sizes are a little small so maybe choose somewhere else if you’re super hungry, but really loved the drinks and apps here.
Depending on your energy levels, hit up a comedy club or one of the many rooftop bars the city has to offer! Spots like London House, Cindy’s Bar, The J. Parker, and Z Bar, are plentiful depending which neighborhood you find yourself in.
Day 3 / Sunday
Sadly you’re probably heading home and winding down from your busy weekend, but hopefully you have time for one more meal!
Head to the Gold Coast area to explore. The whole area is super cute and a great spot to wind down with a coffee and walking around, plus a final brunch at LUXBAR.
I hope you enjoyed your weekend in Chicago! Visiting in the summer is definitely different than visiting in the winter so stay tuned for a winter Chicago guide at some point.