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Four Seasons Hotel

Chicago

Local Time

Local Temperature

21 °C / 70 °F

Couples’ Itinerary

Spring into Chicago List for Couples

If spring is the season of romance, Chicago in spring is the urban romantic’s paradise. This season, discover Chicago alongside your special someone with our suggestions for a perfect couple’s getaway.

Yours to Explore

Romance awaits. Make memories that will last a lifetime with activities that are perfect for couples.

DAY 1

Evening

  • Make it a couple’s treatment and unwind in the Spa with a soothing massage.
  • Blissed out and ready for dinner, head over to Sumi Robata Bar for authentic Japanese cuisine, and sneak down to the 11-seat Charcoal Bar for a handcrafted cocktail. They also have someone dedicated to making your ice cubes!
  • After dinner, pop into the Back Room Jazz Club to hear local talent in the Chicago music scene, or visit the Comedy Bar for some laughs.

 

DAY 2

Morning

  • Breakfast at Yolk, where you don’t have to wait in line if you have a card from our Concierge. You can then join the gallery art walk through the neighbourhood and see what the local artists are producing. 
  • Or, let our Concierge set up a private tour of the Merchandise Mart with a local designer. If you don’t feel like shopping, hang like a Gold Coast local on the patio at Gibson’s and people-watch.

 

Afternoon

  • Head back towards the city to enjoy lunch along the river at Chicago Cut Steakhouse. Even if it’s still too chilly to dine on the patio, their floor-to-ceiling windows will offer the same river views indoors. The house-aged steaks and extensive wine list are the perfect way to while away an afternoon (be sure to save room for the homemade cheesecake!). Want to learn more? Ask for a tour of their ageing room.
  • Or, head towards Lakeview for lunch at Southport Grocery, home to their famous cupcake. After, shop your way down Southport, picking up designer finds at Krista K or sampling wines at Galleria. Bowl the old-fashioned way at Southport Lanes, and stop for a mani-pedi at the best deal in town: TG Nails. Gentlemen will not be left out – guys can enjoy a hot shave down the street at State Street Barbers.

 

Evening

  • Choose a bottle of vino from the Four Seasons cellar and prepare to get creative at local Pilsen Art Gallery, where you can sip and paint as you become the master. Imitate an original painting or create one of your own. For dinner, try Dusek’s – one of the hottest new restaurants in town – and enjoy some punch in their old-fashioned punch bar (you’ll be transported back to the 1920s when the building was built as a dance hall).
  • Or, head to cosy Riccardo Trattoria for mouthwatering Italian specialties. In this small brownstone home, you’ll be transported to Italy, first with their “Buona sera” greeting and then with Chianti, homemade pasta, and the best tiramisu in the city. Cap off the evening with some local rock at Schubas Tavern, a folk rock favourite among local music enthusiasts.
  • Or, taste the latest flavours of South America at Tanta, the hot new Peruvian spot in the city, and follow up the Latin feast with drinks at Celeste, River North’s new art deco-inspired cocktail bar.

 

DAY 3

Morning

  • If you’re the sporty type, start the morning with a running tour of Chicago. Our concierge team can direct you to their favourite routes or set you up with a local running guide. You choose the scenery – lake or city – and get a feel of what it’s like to live in the Windy City.
  • Running not your speed? Walk the Magnificent Mile before the stores open to see the city like a local. Stop at Hendrikx Bakery to stroll with the best croissant in the city, and pop into the 900 Shops for a Metropolis coffee from King Café.   

Afternoon

  • Cab over to Wicker Park for a unique breakfast at an old favourite: Smoke Daddy. (Your morning run or walk made the calories not count!) Here you’ll find old-fashioned biscuits and gravy and the best Bloody Mary in the city, along with a side of blues and an appealing neighbourhood atmosphere.  
  • After breakfast, walk around to discover exciting vintage finds alongside cutting-edge designer boutiques. The Vintage Underground is a treasure trove of costume and designer vintage. Down the street, Mojo Spa creates all their own in-house soaps and lotions. Find the most hilarious baby gear at Psycho Baby. 
  • If shopping is not your thing, take a trip down memory lane at Emporium, a genuine pinball and arcade bar. A Polish beer at local bar Zakopane rounds out the authentic Chicago experience.
  • Have lunch while listening to the blues at Buddy Guy’s Legends. Even on a weekday afternoon you can hear some live blues and sample their southern bar menu.
  • Walk over to the Art Institute through Grant Park to catch the exhibits an hour before closing – and miss the crowds.
     

Evening

  • Now that you’ve enjoyed a local steakhouse meal, learn how to prepare one at the Chopping Block. The lessons learned in this cooking class for two will last beyond your romantic weekend getaway. Learn how to prepare your steak, Caesar salad and chocolate lava cake.

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