What to Do in Chicago Labor Day Weekend 2020, Condé Nast Traveler, September 4, 2020
No doubt Labor Day Weekend looks different this year, but despite 2020's ongoing challenges, Chicago is still the city that works. So for the weekend that symbolizes the last gasp of warm weather before the mercury begins its end-of-year plummet, we think you still deserve a little fun. For 2020, we’re steering readers clear of the usual suspects—the Loop and the Magnificent Mile, where much of recent protest actions and the state’s responses have been at their most concentrated and heightened—in favor of a few adjacent clusters of Chicago’s 77 neighborhoods. Each capsule itinerary suggests a small or independent boutique hotel in the neighborhoods to serve as your home base, and plenty of opportunities for to enjoy the food, arts, and cultural vibrancy for which the city is famous. Read on for what to do in Chicago for Labor Day this year.
Itinerary 1: Hyde Park/Washington Park/Bronzeville/Woodlawn/Jackson Park/Grand Crossing
Where to stay
The Sophy in Hyde Park is right in the heart of the neighborhood. For doorstep proximity to Lake Michigan, try the Chicago Lake Shore Hotel.
Where to eat
Lem’s BBQ in Grand Crossing is a must for rib aficionados. Spot the aquarium-style pit inside while you’re licking your fingers at the ledge. Reggie’s on the Beach at the South Shore Beach House is an oasis of good vibes, with a full bar and food menu—and socially distanced patio. Try B’Gabs for line-down-the-block vegetarian dishes, and Medici for lakeside sandwiches.
What to do
Architecture buffs can walk the University of Chicago campus, and tour Frank Lloyd Wright’s Robie House. Shop one-of-a-kind finds at the Fempowerment Outdoor Thrift Sale on Saturday at The Promontory from 11 a.m. to 3 p.m., with proceeds benefiting the Chicago Alliance Against Racist and Political Repression. Sunday, build a bonfire on Promontory Point—just claim your pit well before sundown.
Itinerary 2: Pilsen, Chinatown, Bridgeport
Where to stay
The new Jaslin Hotel, right in the heart of Chinatown, is perfect for post-dumpling naps.
Where to eat
Chinatown boasts so many great restaurants, including Qing Xian Yuan for dumplings and Joy Yee’s for walkup bubble teas. Our Pilsen picks include 5 Rabanitos and Carnitas Uruapan for a carnivore’s delight. In Bridgeport, check out Maria’s, a bar tucked into an old liquor store with a patio extension. And for something entirely different, try Korean-Polish resto, Kimski.
What to do
Find your chi at Ping Tom Park in Chinatown and take a water taxi up and down the river. In Pilsen, muralism is alive and well—self guided tours encouraged. For the nostalgic among us, The Blues Brothers screens that night at the city’s only drive-in movie at ChiTown Futbol.
Itinerary 3: Lakeview, Boystown, Uptown, Andersonville, Ravenswood, Lincoln Square
Where to stay
Rest up at the LGBTQ-friendly Best Western in Boystown or the charming City Suites in Lakeview.
Where to eat
Off Argyle Street in Uptown, you’ll find craveable banh mi at Ba Le, Malaysian plates at Bingo Tea, and Ethiopian njera with everything on it at Demera. Stop by Filipino-Cuban Bayan Ko in Ravenswood for an ube sundae.
What to do
Visit the outdoor National Cambodian Heritage Museum and Killing Fields Memorial, the only site of its kind outside of Cambodia. Through the weekend, film buffs can head to Lakeview’s Music Box Theatre, which features Christopher Nolan’s Tenet in 70mm; their outdoor Garden Movies series features the Charlie Chaplain movie City Lights each night at 7:45. The pre-Prohibition-era Green Mill Cocktail Lounge is still the boite de nuit for live jazz (note that there is very limited capacity right now).
Itinerary 4: Garfield Park, Humboldt Park, Wicker Park, Logan Square
Where to stay
Logan Square’s Longman & Eagle or Wicker Park’s The Robey.
Where to eat
Humboldt Park is Chicago’s answer for Boriqueños feeling sick for home. Whether that's you or not, you still must eat the Chi-Rican creation the jibarito—a sandwich of flattened and fried plantains, with lots of garlic and pork; Jibaritos Y Mas and other fine restaurants off of Paseo Boricua (or, W. Division Street) do fine versions. Logan Square boasts may of the city’s food gems, including vegetarian-friendly Lula Cafe, and Cellar Door Provisions for bread and pastry lovers, and the award-winning Mi Tocaya Antejoria shows off dishes from loads of different regions in Mexico. Over in Wicker Park, Nawlins is callin’ with po’ boys galore at Ina Mae Tavern & Packaged Goods.
What to do
The outdoor portion of the Garfield Park Conservatory welcomes visitors, RSVP recommended. Walk under the El to the Garfield Park Fieldhouse and admire its golden dome. Stroll Humboldt Park to see its lagoon surrounded by prairie wildflowers, and enjoy the rental swan paddle boats. The 606, a three-mile corridor converted from an old freight train passage, gives wanderers a glance at the fabric of each neighborhood.
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