Italian with a modern twist, Monteverde is helmed by Top Chef alum Sarah Grueneberg and known for its hand-made fresh pastas like the cacio e pepe and raviolo. This is our favorite resultant in the city - make sure to book reservations early!
A dimly-lit, speakeasy-style steakhouse serving prime cuts, seafood towers, and strong cocktails. It’s the perfect blend of swanky and soulful, with jazz playing in the background and butter-soaked everything on the menu. Our favorite steakhouse in the city!
A bright and airy Mediterranean spot with coastal Californian vibes, Ema offers shareable dishes like house-made hummus, lamb kefta, and honey-roasted carrots. One of Jess's all time favorites in Chicago!
Sleek and modern, RPM Italian is a Lettuce Entertain You concept co-founded by Giuliana and Bill Rancic. Known for its upscale takes on Italian classics like truffle-studded pasta and slow-roasted meats, it’s ideal for a dressed-up dinner.
This bold, upscale steakhouse pairs luxury with irreverence—expect high-end meats, seafood towers, and a martini cart, all in a glam setting. Their “I Don’t Give a F*@k” tasting menu is both iconic and indulgent.
Romantic and candlelit, Gilt Bar serves elevated American comfort food like truffle pasta and roasted bone marrow. With vintage vibes and a tucked-away basement bar, it’s a hidden gem for late-night drinks too. One of Matt's all time favorite restaurants!
A stylish Japanese restaurant offering sushi, robata-grilled meats, and creative cocktails in a mid-century Tokyo-inspired setting. Their downstairs Izakaya bar is a great place to linger post-dinner (The Izakaya is Matt's favorite cocktail bar in the city)!
Bright, lively, and great for groups, Alla Vita serves approachable Italian fare like wood-fired pizzas, burrata, and house-made pastas. Its name means "to life," and the vibe matches: cheerful and celebratory.
Chef Stephanie Izard’s Chinese-inspired hotspot features bold flavors, handmade noodles, and dim sum with a twist. The eclectic décor and signature duck fried rice make this a West Loop standout.
Tucked away in a cobblestone alley, Trivoli Tavern is a moody, clubby tavern with a menu full of steaks, oysters, and hearty mains. It’s ideal for a cozy dinner or celebratory drinks in a plush leather booth.
Jess and Matt's cozy neighborhood staple in Old Town, Topo Gigio serves up classic Italian dishes like veal limone, seafood pastas, and wood-fired pizzas. With a lively patio and warm, old-school vibes, it’s perfect for a relaxed, delicious dinner just steps from Second City.
A fourth-generation Italian grocer turned sandwich legend, JP Graziano’s is famous for its spicy Mr. G sandwich and housemade giardiniera. Matt's go-to sandwich (and lunch spot) in the city!
No-frills and all flavor, Mr. Beef is a Chicago institution for Italian beef sandwiches so good, it inspired Hulu’s The Bear. Go dipped, with hot or sweet peppers, and thank us later.
One of Matt and Jess’s favorite casual spots, Athenian Room is a low-key Greek gem known for its legendary chicken kalamata and crave-worthy fries. It’s cash-only, no-frills, and totally worth it, just ask Tina Fey (seriously, she’s obsessed).
Home to what’s often called the best burger in America, Au Cheval is a must-visit diner with upscale bar food and rich, indulgent eats. Be prepared for a wait (often 1 - 2 hours), but it’s absolutely worth it.
Known for its caramelized crust, Pequod’s deep-dish pizza is a true Chicago original. It’s not fancy, but it might just ruin all other pizza for you. Matt and Jess's favorite deep-dish style pizza in the city!
Texas-style BBQ served in a casual, warehouse-style space tucked behind an alley. Expect brisket by the pound, cold beer, and picnic tables.
With sweeping views of Millennium Park and Lake Michigan, Cindy’s offers seasonal American fare and craft cocktails in a glass atrium. Come for the views, stay for the frosé.
Perched atop a historic hotel, this rooftop bar offers panoramic views of the Chicago River, skyline, and lake. It’s a popular spot for celebratory cocktails, especially around sunset.
This is a can’t-miss and one of our favorite spots to grab a drink and soak in Chicago life. Located right on the Riverwalk, it’s perfect for casual bites, people-watching, and sunny-day cocktails by the water.
Perched atop the Hotel Lincoln, The J. Parker offers panoramic views of Lincoln Park, the lake, and the city skyline, all with a cocktail in hand. It’s a perfect sunset spot and one of our favorite rooftops to toast the weekend.
A charming French-inspired bakery and café serving up buttery croissants, flaky pastries, and artisanal breads baked fresh daily. It’s a favorite local spot to enjoy a leisurely breakfast or grab a coffee and pastry while exploring the lively Old Town corridor.
Just steps from where we live, Doma Cafe is our go-to spot for expertly crafted coffee, fresh pastries, and delicious breakfast sandwiches. With its cozy, laid-back vibe, it’s the perfect place for a morning pick-me-up or an afternoon recharge.
A beloved coffee destination known for its bold blends and signature draft lattes. Jess is obsessed with the vanilla dairy draft latte, it's her go-to pick-me-up. Perfect for grabbing coffee to-go while exploring the Gold Coast neighborhood and enjoying a stroll.
A vibrant bakery and café known for its decadent cakes, flaky pastries, and thoughtfully brewed coffee. It’s the perfect spot to satisfy your sweet tooth or grab a delicious breakfast sandwich right in the heart of the Loop.
A sleek, minimalist café offering meticulously brewed coffee and expertly crafted espresso drinks. Perfect for a quick caffeine boost with stunning views of the Chicago River and city skyline right from Wolf Point Plaza.
A classic Chicago experience, Shoreline offers architecture boat tours and lake cruises that give you stunning views of the skyline and fascinating stories behind the city's most iconic buildings. It’s a fun, relaxing way to learn a bit and fall in love with the city from the water. Matt and Jess have a combined tally of 6 Chicago River Architecture Tours, so you know it’s good!
Stretching along the south bank of the Chicago River, the Riverwalk is a scenic pathway lined with cafes, bars, public art, and stunning views of the city’s architecture. It’s the perfect place for a stroll, a drink by the water, or just taking in the energy of downtown Chicago.
A lively lakefront destination with shops, restaurants, a giant Ferris wheel, and unbeatable lake views. Whether you're catching fireworks, hopping on a boat ride, or just going for a walk, Navy Pier is one of Chicago’s most iconic spots.
Easily accessible from downtown (including right off Michigan Ave near Oak Street Beach), the Lakefront Trail is an 18-mile paved path that hugs Lake Michigan and winds through parks, beaches, and some of the city’s best skyline views. Whether you're walking, running, or biking, it’s one of the best ways to experience the beauty of Chicago’s lakefront.
Still “Sears Tower” in the hearts of many locals, this iconic skyscraper offers breathtaking views from the Skydeck on the 103rd floor. Step out onto The Ledge, a glass box extending over the city, for a thrilling (and slightly terrifying) photo op.