Sandwich shop · Loop
3
Chicago’s sandwich powerhouse still rolls with its truck: truffle BLTs, buffalo chicken, and perfect fries. Regular at the city’s Daley Plaza Food Truck Fest and a frequent brewery pop-up guest, it’s a reliable downtown lunchtime win.
Italian restaurant · Near North Side
Italian marketplace with restaurants, wine bar, bakery, and gelato
18 Postcards
Bar · Loop
Vast cider selection, live music, and Chicago dogs on the river.
14 Postcards
Italian restaurant · Little Italy
Traditional Italian fare, huge portions, old school vibe
3 Postcards
Cafe · Near West Side
Italian cafe serving sandwiches, coffee, pastries, and gelato
Barbecue restaurant · Little Italy
House-smoked meats, craft beer, updated sides, and booze
15 Postcards
Thai restaurant · Ravenswood
Authentic Thai dishes, vegetarian options, BYOB, Tigers steak
2 Postcards
Fine dining restaurant · Uptown
Inventive tasting menus with creative vegan options
British restaurant · Avondale
Creative British pub grub & a huge beer selection with fireplace
19 Postcards
Cocktail bar · West Town
Parisian-inspired cocktail bar with a standout martini program
7 Postcards
International airport · Chicago Midway International Airport
Airport with direct train to Chicago, many food options