Our Favorite Activivities
The Art Institute of Chicago: home to American Gothic, A Sunday on La Grande Jatte, and a whole lot more than just famous paintings. It’s where art history meets Chicago’s history, and trust us, it’s worth the visit.
Hop on the Chicago Architecture Tour and discover why our skyline is so unique. From the Sears Tower to Wright’s masterpieces, it’s the best way to experience the city’s architectural beauty.
Chicago’s comedy scene shines at legendary spots like The Second City, Zanies, Comedy Bar, The Lincoln Lodge, and Laugh Factory, offering a mix of improv, stand-up, and sketch. With top talent and intimate settings, these venues guarantee unforgettable laughs.
For outdoor pickleball in Chicago, Big City Pickle features well-maintained courts in the heart of the city, offering a vibrant setting for casual games or competitive play. For indoor play, SPF provides a top-tier, climate-controlled environment, perfect for year-round action and skill development if you’re feeling active.
A stroll along the Chicago Riverwalk or Lakefront Trail is the perfect way to experience the city’s vibrant energy and natural beauty, with plenty of spots to stop at riverside cafes, lively bars, or art installations.
Timeout Market Chicago, located in the Fulton Market District, is a bustling food hall featuring top local chefs and diverse dining options. It combines great food, creative cocktails, and a lively atmosphere, making it a popular spot for both locals and visitors.
Our Favorite Bites
The Bellevue, located in Chicago's ‘Viagra Triangle’, is a trendy, upscale restaurant and bar offering a lively atmosphere, right in the heart of some of the best shopping in Chicago.
Pizzaria Portofino offers a stunning dining experience right on the river. Whether you're enjoying a fresh pizza on the outdoor patio or savoring a glass of wine by the water, the riverside location creates a perfect backdrop for a memorable meal.
Ramen-San offers a warm and inviting atmosphere with delicious bowls of ramen, featuring rich broths, tender noodles, and a variety of creative toppings, making it a perfect spot to unwind and enjoy a comforting meal.
Cindy's Rooftop is home to one of the best skyline and Millennium Park views in the city. They’re known for serving up craft cocktails and seasonal dishes in a relaxed yet chic setting. Reservations fill up quick!
Quartino is a lively Italian restaurant known for its small plates designed for sharing. Offering a variety of pizzas, pastas, and wines, it creates a casual yet delicious dining experience ideal for groups.
The Smith is a lively, upscale American restaurant offering a menu that combines classic comfort foods with modern twists, alongside creative cocktails right in the heart of River North. A regular stop when we lived across the street!
Our Favorite Sips
The Guinness Open Gate Brewery is a unique spot where you can enjoy a classic pint of Guinness along with some Chicago specials. It's perfect for grabbing some apps and enjoying a laid-back atmosphere with friends.
Z Bar is situated atop The Peninsula, offering an upscale rooftop experience. The bar is known for its sleek, modern design, making it the perfect spot for an overpriced cocktail.
Guilt Bar is a cozy, upscale lounge known for its intimate ambiance and creative cocktails, often serving as a hidden gem for those seeking a refined yet relaxed drinking experience.
The Allis at Soho House is a vibrant café and lounge offering a relaxed atmosphere with modern, cozy décor. It serves a variety of dishes, coffee, cocktails & mocktails.
Streeter's Tavern is a classic dive bar nestled in a cozy basement. It's a great spot to play darts and grab a beer or two.
The Shamrock Club is an Irish-American bar, known for its lively atmosphere. A great spot to bar stool, eat popcorn and pay pool.