Things To Do
Architecture River Tour
The Architecture River Tour in Chicago offers a unique perspective on the city's iconic skyline and architectural history, featuring over 40 landmarks along the Chicago River.
Chicago Riverwalk
Walk up and down the riverwalk, sip wine at City Winery, frozen cocktails at Tiny Tapp, and watch the boats go by! The 1.25-mile path stretches along the south bank of the Chicago River, right through the heart of downtown and is easy to access from many downtown streets — just look for the staircases at Michigan Ave, Wabash, Clark, LaSalle, and Franklin.
Navy Pier
Dining, shopping, attractions and rooftop bar (Offshore).
Pizzeria Portofino
Located directly on the Chicago riverfront, Pizzeria Portofino is a casual restaurant offering hand-stretched pizzas, coastal wines, spritz, best parmesan fries and an expansive patio! Recommend making a reservation in advance.
La Scarola
Our favorite Italian restaurant! Authentic, old-school vibes. Low-key, casual, but brings in celebs and high-profile diners. Big portions for low cost :) Call in advance for a reservation.
Trivoli Tavern
A cozy, romantic spot and one of our go-to favorites. If the weather allows, the string-lit cobblestone patio feels straight out of Italy and pairs perfectly with their Happy Hour (M-F, 4-5 pm). Don’t miss the dirty or espresso martinis, hot chicken sliders, vodka rigatoni, wagyu burger, or the sticky date cake. Reservations open 21 days in advance, with new dates released at 9 a.m., so set your alarm & calendar to snag a table. If you can't get a reservation in advance, put your name down early and walk across the street over to Fox Bar or The Allis and have a drink while you wait!
Gibsons Bar & Steakhouse
A classic Chicago steakhouse in a lively neighborhood, known for excellent steaks and standout desserts. The bar, complete with live piano music, is a great spot for a nightcap. Recommend making a reservation in advance.
Pequod's Pizza
Chicago's best deep dish pizza (in our opinion!) Recommend making a reservation in advance. Other Chicago Deep Dish Places: - Lou Malnati's - Gino's East - Giordano's
La Josie
An award-winning Mexican restaurant with an agave bar, rooftop and the best steak tacos and freshest guac (get the seasonal fruit one plus the traditional!) Recommend making a reservation in advance.
Momotaro
A modern Japanese restaurant with unique cocktails, small plates and fresh sushi. The Beef Tsukune Sliders are a must! Recommend making a reservation in advance.
London House Rooftop
London House Rooftop offers unbeatable views of Chicago’s skyline. Grab a seat, order a cocktail and share a few apps! Some other favorite rooftops in the city: - Cindy's: expansive look at Millennium Park, the Bean and the lake - The J Parker: views of the city and Lincoln Park - Upstairs at the Gwen: unique views of the city
Clover Sports and Leisure
Our favorite local sports bar! Lots of TVs, darts, pop a shot (Tom is definitely the record holder for most rounds played), pool table and free popcorn machine.
