Chicago's downtown grid under the elevated tracks. Lunch counters serve the office crowd; Italian Village has run since 1927 and Lou Mitchell's since 1923.
Pizano's Pizza & Pasta in Chicago is the family-owned Loop deep-dish room founded in 1991 by Rudy Malnati Jr., son of Pizzeria Uno's original cook Rudy.
OrderThe cheese deep-dish, no toppings, the way Rudy Sr. baked it at Uno.
TipThe Madison location is the original; State Street is the bigger pre-theatre spot.
Three days at McCormick Place in late April. The South Loop fills and Chinatown, one stop down the Red Line, takes the overflow.
TipChinatown is a ten minute ride from McCormick and keeps serving long after the show floor closes.
Buddy Guy's Legends in Chicago is the South Wabash blues room the man himself opened in 1989 and where he still plays a residency every January.
TipClosed Monday and Tuesday. Wednesday and Thursday close at midnight; weekends run to 01:30. Cover usually $20, kitchen serves Louisiana barbecue.
Cindy's rooftop in Chicago sits on the 13th floor of the Chicago Athletic Association with all-season terrace seating that frames Millennium Park and Lake Michigan.
TipWeekends fill from 21:00; reserve via OpenTable or arrive at 16:00 for the sunset window. The terrace stays heated and open year-round.
LH Rooftop in Chicago crowns LondonHouse on the corner of Wacker and Michigan with three tiers of terrace facing the river and the Trump Tower clock face.
TipOpen every day until midnight, food last call 22:00. The top tier is the photo spot; weekend brunch from 11:00 is the easy walk-in window.
Private tour · 2 hours
Short on time? Discover Chicago’s food, stories, and local life on this small-group Loop walk. Perfect for first-time visitors with iconic bites and insider tips in 2 hours.
Guided tour · 3 hours
Discover Chicago’s trendiest dining scene on a guided walk. Taste chef-driven dishes, sip craft brews, and explore West Loop’s hidden gems.
Guided tour · 3 hours
Taste Chicago’s iconic foods on this Loop District tour! Deep dish pizza, Italian beef, gourmet popcorn and more tastings, plus our delicious Secret Dish!
