Elevated City Guides: Chicago
Looking for a fun weekend getaway? Look no further than the Windy City, a.k.a. Chicago! Having lived there for almost a decade, the city has a soft spot in my heart. It has incredible restaurants, a fun sports scene, plus world-renowned shopping, a vibrant theater district, Lake Michigan, and much more.
Best time to visit: May + October
Avoid: January + February
Chicago is a wonderful city. It’s cleaner and more accessible than New York, less sprawling than L.A., and if it does one thing better than the rest, it’s food and drink. It would take a novel to recommend all the great places to eat, so here are my recent favorites.
Best Restaurants:
Italian: Monteverde (make a reservation months out), Siena Tavern (order the coccoli and the meatball)
Mediterranean: Aba, Ema (sister restaurants, Aba has a rooftop), Fig & Olive (high-end and delicious)
Asian: High Five Ramen (put your name in and go get drinks while you wait 3 hours), Kyoten (omakase tasting menu for the real sushi connoisseurs)
Steak: Chicago Cut (classic), Bavette’s (best), GT Prime (modern, elevated)
Burgers: Au Cheval (prepare to wait, but it’s worth it), Smyth and the Loyalist (go downstairs to the tavern-area and order the burger)
Famous: Girl & the Goat (approachable, delicious), Alinea (culinary tasting menu)
Pizza: Piquod’s (chicago deep-dish), Parlor (not deep dish)
Other: Bub City (BBQ and vibes), Ranalli’s (the best chicken tenders you’ve ever had)
Best Bars (all of the above restaurants have good bars, too!):
Oakville Cellars - new spot for wine tasting, West Loop
Aviary - elevated, intricate cocktails
Scofflaw - low key vibe for detailed cocktails
Gilt Bar - beautiful bar, delicious drinks
Celeste - multi-floor venue with a garden rooftop, a middle club, and a downstairs bar
Cabra - pool-side rooftop bar (good lobby bar here, too)
Federales - tequila and shot glasses made from ice? Say less.
Kaiser Tiger - German-inspired beer garden with curling during the colder months
Franklin Room - all the whiskeys and bourbons your heart could desire
There is SO much to do in Chicago! Pick a few of your faves and buy tickets ahead of time.
Favorite Activities:
Architecture Tour on the Chicago River - do not skip this!
Boat Rental on Lake Michigan
Attend a game: Cubs, Bears, BlackHawks, Bulls
Shop along Michigan Avenue and in Gold Coast
Attend a comedy show at Second City, Zanies, or a headline performer at the Chicago Theater (Chicago comedy scene is known for its many Saturday Night Live alums)
Walk along the River Walk
There are a number of Hilton/Marriott properties, but I’d recommend staying in the neighborhoods of West Loop or River North rather than the Loop/business district.
Where to stay:
West Loop: the Hoxton Hotel
River North: the Thompson Hotel or London House Chicago
Happy travels!
Hannah
