It’s said that Chicago is America’s most dichotomous city. It’s a place where a punishing winter meets a baking summer. Where high and historic museum art collides with ostentatious public street art. Where cutting-edge culinary-wheel-reinventing restaurants sit side by side with parlours serving pizza in a pan so deep you wonder if you’ll ever reach the bottom.
No matter what time of year you visit, discover Chicago with our full day, weather-proof, eating, shopping and sightseeing itinerary.
Search Flights To ChicagoStop 1: Jump on the Blue Line “EL” train to Logan Square. Enjoy a brunch of local and organic cuisine at Lula Café (2537 N. Kedzie Boulevard). Drop in Wolfbait & B-Girls (3131 West Logan Boulevard) for locally designed clothes, cool accessories and postcards.
Stop 2: Stroll for 20 minutes south down Milwaukee Avenue towards Bucktown. Try on a few high-end designer duds at Scoop (1702 N. Milwaukee Avenue) and thrifty finds at Una Mae’s Freak Boutique (1528 N. Milwaukee Avenue). Immerse yourself in the city’s cool, edgy and sometimes gritty hipster scene with a wander to Wicker Park and the “Six Points” intersection. Expand your music horizons at Reckless Records (1532 N. Milwaukee Avenue) and then stop by Big Star (1531 N. Damen) for a beer or a margarita.
Stop 3: Walk down Damen Avenue to check out the hip boutiques on Division Street in Wicker Park. Stop 3: Walk down Damen Avenue to check out the hip boutiques on Division Street in Wicker Park. Pick up a few one-of-a-kind pieces by local, unknown designers at Penelope’s (1913 West Division Street) to fill out your wardrobe, and then refuel with a coffee and cookie from the Alliance Bakery (1736 W. Division Street), or a frozen yoghurt at Starfruit (1745 W. Division Park).
Stop 4: Head east down Division Street for a few minutes and hop on the Blue Line at Milwaukee for the 15-minute ride downtown to Monroe. Cast your eye on the city’s best collection of impressionist and modern art at the Art Institute and Modern Wing (111 South Michigan Avenue). Walk through the gorgeous Millennium Park (201 East Randolph Street) before enjoying an inexpensive and re-energizing massage by a massage student at the Cortiva Institute (17 N. State Street).
Stop 5: Stroll towards the Chicago River to claim your pre-booked spot on the 90-minute Architectural Cruise on board Chicago’s other First Lady. When you’re back on dry land, it’s just a few minutes’ stroll up Michigan Avenue to Purple Pig (500 N. Michigan Avenue), where you can settle in for a dinner of chicken thigh kebabs.
Stop 6: If it’s warm, enjoy alfresco sundowners on the Roof at The Wit Hotel (201 N. State Street). If it’s cold, catch a concert or live comedy show at the Chicago Theatre (175 N. State Street). And do not miss a chance to cap it all off with late-night cocktailing at Double A at Mercadito (108 W. Kinzie), located just a 10-minute walk across the river.
Cheap Flights To ChicagoWritten by insider city guide series Hg2 | A Hedonist’s guide to…
(Image: þeodriċ æðelfriþ)
