A Summer Weekend in Chicago | June 24th 2023

Hi Jess and Alex,

I'm so thrilled that you'll be visiting me in Chicago the weekend of June 24th, 2023! I've put together a list of suggestions tailored to your interests, including where to eat, what to do, and options for places to stay. I've also added a sections on must-see rooftops, riverside drinks, noted reservation recommendations, and provided some ideas for photos you can use in your IG photodump. Additionally, I've included information on a local street fair happening during your visit. I hope you find these suggestions helpful and I can't wait to see you!

Where to Eat

  • Bavette's Bar & Boeuf

    • Why we like it: This upscale steakhouse offers a cozy, speakeasy vibe and serves some of the best steaks in town. Don't miss their mouth-watering bone-in ribeye and the decadent chocolate cream pie for dessert. Reservations recommended.

    • Photo idea: Capture the vintage ambiance of the restaurant, including the dimly lit dining room and the classic bar area.

  • Big Star

    • Why we like it: This lively spot in Wicker Park is perfect for tequila lovers, with an extensive selection of tequilas and delicious tacos. Enjoy their dog-friendly patio while sipping on a refreshing margarita.

    • Photo idea: Snap a photo of the colorful taco plates and the vibrant outdoor patio.

  • City Winery Chicago

    • Why we like it: For wine enthusiasts, City Winery offers a unique urban wine experience with a variety of wines on tap and a delicious menu to pair with your favorite glass. Reservations recommended.

    • Photo idea: Take a picture of the wine barrels and the cozy interior, showcasing the urban winery atmosphere.

Chicago Classics: Pizza, Hot Dogs & Street Food

  • Portillo's

    • Why we like it: A Chicago institution, Portillo's is known for its delicious hot dogs, Italian beef sandwiches, and chocolate cake shakes. It's a must-try for anyone looking to experience authentic Chicago street food.

    • Photo idea: Capture the iconic hot dog and Italian beef sandwiches, as well as the lively atmosphere of the restaurant.

  • Lou Malnati's Pizzeria

    • Why we like it: Lou Malnati's is famous for its deep-dish pizza, which features a buttery crust, rich tomato sauce, and gooey cheese. A visit to Chicago wouldn't be complete without trying this classic dish.

  • Garrett Popcorn Shops

    • Why we like it: Garrett Popcorn is a beloved Chicago snack, offering a variety of gourmet popcorn flavors. Their signature "Garrett Mix" combines sweet CaramelCrisp and savory CheeseCorn, creating a delicious and addictive treat.

    • Photo idea: Capture the colorful popcorn tins and the variety of popcorn flavors available at the shop.

  • The Wiener's Circle

    • Why we like it: Known for its late-night eats and entertaining staff, The Wiener's Circle is a Chicago staple for hot dogs, burgers, and cheese fries. It's a unique experience that's perfect for a late-night snack after a night out in the city.

What to Do

  • The Art Institute of Chicago

    • Why we like it: This world-renowned museum houses an incredible collection of art, perfect for capturing stunning photos. Don't miss iconic works like Grant Wood's "American Gothic" and Georges Seurat's "A Sunday on La Grande Jette."

    • Photo idea: Capture the exterior of the museum, including the famous lion statues, as well as some of the iconic art pieces inside.

  • Millennium Park

    • Why we like it: This iconic park is home to the famous "Bean" sculpture, as well as beautiful gardens and stunning views of the city skyline. While you're there, stop by the nearby Maggie Daley Park for more outdoor fun.

    • Photo idea: Take a classic photo of the reflective "Bean" sculpture, as well as shots of the lush gardens and skyline views.

  • Montrose Dog Beach

    • Why we like it: This off-leash dog beach is a great spot to spend a sunny afternoon with your furry friends. Enjoy the beautiful lakefront views and snap some adorable photos of your pups playing in the water.

    • Photo idea: Capture your dogs splashing in the water and playing with other pups, as well as the scenic lakefront background.

  • Chicago Architecture River Cruise

    • Why we like it: This relaxing boat tour offers stunning views of Chicago's skyline and provides fascinating insights into the city's rich architectural history, perfect for capturing amazing photos. Reservations recommended.

    • Photo idea: Take photos of the unique architectural styles and iconic buildings along the river, as well as the skyline views from the boat.

  • White Sox Game

    • Why we like it: You already have tickets to the White Sox game on Saturday, 6/24! Enjoy America's favorite pastime and don't forget to try some classic ballpark snacks like hot dogs and nachos.

    • Photo idea: Capture the excitement of the game with action shots, as well as photos of the stadium and the classic ballpark food.

Must-See Rooftops

  • Cindy's Rooftop

    • Why we like it: Located atop the Chicago Athletic Association Hotel, Cindy's offers panoramic views of Millennium Park and Lake Michigan. Enjoy craft cocktails and delicious bites in this stylish rooftop setting. Reservations recommended.

    • Photo idea: Snap a photo of the stunning views from the rooftop, as well as the stylish interior and craft cocktails.

  • LondonHouse Chicago

    • Why we like it: This tri-level rooftop offers breathtaking views of the Chicago River and skyline. Sip on a cocktail while lounging in the elegant rooftop bar or the outdoor terrace. Reservations recommended.

    • Photo idea: Capture the stunning river and skyline views, as well as the elegant rooftop lounge and terrace.

  • The J. Parker

    • Why we like it: Perched atop the Hotel Lincoln, The J. Parker offers stunning views of Lincoln Park and Lake Michigan. Enjoy creative cocktails and tasty bites in this chic rooftop lounge. Reservations recommended.

    • Photo idea: Take photos of the panoramic views of Lincoln Park and Lake Michigan, as well as the stylish lounge area.

Riverside Drinks

  • City Winery at the Riverwalk

    • Why we like it: Located right on the Chicago Riverwalk, this outdoor extension of City Winery offers a picturesque setting to enjoy a glass of wine and a bite to eat while taking in the beautiful river views.

    • Photo idea: Capture the bustling atmosphere of the Riverwalk and the scenic views of the river and surrounding buildings.

  • Tiny Tapp & Café

    • Why we like it: This cozy café and bar on the Riverwalk offers a laid-back atmosphere to enjoy craft beers, cocktails, and delicious food while soaking in the stunning river views.

    • Photo idea: Snap a photo of the charming café seating and the beautiful backdrop of the river.

Local Street Fair

  • Wicker Park Fest

    • Why we like it: Taking place the weekend of your visit, Wicker Park Fest showcases the neighborhood's vibrant culture with live music, local food, unique vendors, and art installations.

    • Photo idea: Capture the lively atmosphere of the festival, including the bustling crowds, colorful food stands, and artistic installations.

Options to Stay

  • The Langham, Chicago

    • Why we like it: This luxurious hotel offers an exceptional experience with its elegant rooms, award-winning spa, and prime location near the Magnificent Mile.

  • The Robey

    • Why we like it: Located in the trendy Wicker Park neighborhood, this boutique hotel offers stylish rooms and a rooftop lounge with panoramic city views. Plus, it's just a short walk away from Big Star, perfect for tequila lovers!

  • W Lakeshore

    • Why we like it: This stylish hotel offers stunning views of Lake Michigan and Navy Pier, modern rooms, and a chic rooftop bar. It's located just steps away from the lakefront and the Magnificent Mile.

  • HI Chicago Hostel

    • Why we like it: For budget-conscious travelers, this hostel offers clean and comfortable accommodations in a convenient downtown location.

  • LondonHouse Chicago

    • Why we like it: This luxurious hotel is located in a historic building along the Chicago River, offering elegant rooms, a tri-level rooftop lounge with stunning views, and a prime location near the Magnificent Mile. It's also home to one of the must-see rooftops mentioned earlier, making it a perfect place to stay for an unforgettable Chicago experience.

I hope these suggestions help make your first visit to Chicago a memorable one. If you have any questions or need more recommendations, please don't hesitate to reach out. See you soon!

Nick & Lulu