Menu
  • Couple Shopping

    48-HOUR ROMANCE

    Fall in love with this travel itinerary filled with romantic things to do in Chicago. View our...

  • The 606

    48-HOUR ROMANCE

    Fall in love with this travel itinerary filled with romantic things to do in Chicago. View our...

  • Celeste

    48-HOUR ROMANCE

    Fall in love with this travel itinerary filled with romantic things to do in Chicago. View our...

  • The Magnificent Mile Chicago

    48-HOUR ROMANCE

    Fall in love with this travel itinerary filled with romantic things to do in Chicago. View our...

Fall in love with Chicago and experience Lake Michigan's shoreline, The Magnificent Mile and an unforgettable gourmet meal.

 

 

DAY  1

Chopping Block Cooking Class

 

MORNING

❏ Start your day at Café Selmarie and order some fruit-filled heart-shaped cookies for dessert.

❏ After breakfast, take a cooking class at the Chopping Block and see what kind of gourmet dishes you can create together.

 

AFTERNOON

❏ Snuggle up and take a carriage tour of Michigan Avenue.

 

EVENING

❏ Have an intimate dinner at the exotic Argentine-inspired La Sirena Clandestina.

❏ Check into the Four Seasons Hotel Chicago and indulge in a couples' Skylight Swim at the spa, complete with a swim under the stars, champagne and canapes.

 

 

DAY 2

Divvy

 

MORNING

❏ Order a romantic breakfast in bed at the Four Seasons. Indulge in red velvet pancakes topped with chocolate, strawberries and mascarpone cream and wash it down with a mimosa.

❏ Then, weather permitting, rent a Divvy Bike and pedal alongside Lake Michigan or The 606, a new elevated trail that weaves through various neighborhoods.

 

AFTERNOON

❏ Take in extraordinary views of Lake Michigan while lunching on fine Italian cuisine at Spiaggia.

❏ Do a little couples shopping on The Magnificent Mile and maybe binge on a new bauble at Tiffany & Co. or Cartier.

❏ Enjoy sweets with your sweetie at Candyality in Water Tower Place. Pick your favorite treats and let the Candy Specialists tell you what your choices say about your personality.

 

EVENING

❏ Have dinner at North Pond. Located in Lincoln Park, it boasts postcard-perfect views of Chicago's skyline.

❏ Top off your dreamy evening with some fabulous music at Andy's Jazz Club & Restaurant.

❏ Stop by refined River North cocktail bar Celeste for a nightcap.

 

ADD A DAY & STAY

Art Institute Modern Wing

 

MORNING

❏ Forget about the diet. Order some luscious caramelized apple and pecan French toast at Eggsperience.

❏ Spend the morning with the Impressionists at the Art Institute of Chicago and then ooh and aah over the contemporary masters in the Modern Wing.

 

AFTERNOON

❏ Take a spin on the Navy Pier Ferris Wheel or bowl and visit the arcade at Lucky Strike and FTW.

 

EVENING

❏ Share a bottle of wine and dip bread, cheese and other morsels at Geja's Café. Finish it off with some chocolate fondue.

❏ Continue your date with live music and libations at Untitled Supper Club.

❏ Spend the night at the sleek and zen-like dana hotel and spa and order a bottle of champagne and some strawberries for a goodnight snack.

 

Plus... Coffee and Dessert: 5 Neighborhood Sweet Spots

 

Bang Bang Pie & Biscuits

 

 

  1. Opened in 1922, Dinkel's Bakery looks like something out of the ‘50s. Because of the Dinkels' German heritage, tortes and strudels are tops here. Find them in Lakeview.
  2. It's the Princess Torte, a whipped cream and vanilla custard-filled three-layer yellow cake with marzipan (available by the slice) that lures customers to 80-year-old Swedish Bakery in Andersonville.
  3. Bang Bang Pie & Biscuits started out as a food truck. Now customers get their Key lime pie served on a paper plate atop a blue checkered napkin indoors in Logan Square.
  4. Artopolis Bakery & Café in Greektown earns raves from critics. The café has a full menu, including pizza and martinis, but locals know to come for Greek pastries like baklava.
  5. Lincoln Park's Floriole Café & Bakery is best known for French pastries like Gâteau Basque, an almond cake filled with cream and fruit.

 

Drinks with a View

Matt Kirouac

 

❏ Linger at Rebar, a high-end lounge in the Trump Hotel Chicago offering specialty cocktails, small plates and skyline views.

The Signature Lounge at the 96th floor of the John Hancock Center is the place for a drink after sundown.

❏ Sip a handcrafted cocktail on the rooftop of Hotel Lincoln at J. Parker.

❏ Enjoy the ambiance and libations at another rooftop bar like the clubby, indoor drumBAR, or Vertigo Sky Lounge where you'll find some of the city's best DJs.

❏ Barhop at other hot-right-now indoor-outdoor rooftop lounges like I|O Urban Roofscape atop the Godfrey Hotel Chicago or ROOF at theWit Hotel Chicago.

 

Related Listings

 

Navy Pier
600 E. Grand Ave.
Chicago, IL 60611
(312) 595-5300

Candyality
835 N. Michigan Ave.
Chicago, IL 60611
(773) 472-7800

dana hotel and spa
660 N. State St.
Chicago, IL 60654
(312) 202-6000

theWit Chicago – A DoubleTree By Hilton Hotel
201 N. State St.
Chicago, IL 60601
(312) 467-0200

Hotel Lincoln
1816 N. Clark St.
Chicago, IL 60614
(312) 254-4700

Untitled Supper Club
111 W. Kinzie St.
Chicago, IL 60654
(312) 880-1511

Divvy
658 N. Milwaukee Ave.
Chicago, IL 60647
(855) 553-4889

Art Institute of Chicago
111 S. Michigan Ave.
Chicago, IL 60603
(312) 443-3600

ROOF on theWit
201 N. State St.
Chicago, IL 60601
(312) 239-9502

Related Articles

THE ULTIMATE CHICAGO BUCKET LIST

The Magnificent Mile® Association
625 N. Michigan Ave., Ste. 401
Chicago, IL 60611
(312) 642-3570

Geja's Café
340 W. Armitage Ave.
Chicago, IL 60614
(773) 281-9101

Four Seasons Hotel Chicago
120 E. Delaware Pl.
Chicago, IL 60611
(312) 280-8800

Trump International Hotel & Tower Chicago
401 N. Wabash Ave.
Chicago, IL 60611
(312) 588-8000

Lucky Strike Lanes
322 E. Illinois St.
Chicago, IL 60611
(312) 245-8331

The Godfrey Hotel Chicago
127 W. Huron at LaSalle
Chicago, IL 60654
(312) 649-2000

Celeste
111 W. Hubbard St.
Chicago, IL 60654
(312) 828-9000

La Sirena Clandestina
954 W. Fulton Market
Chicago, IL 60607
(312) 226-5300

Spiaggia Restaurant and Lounge
980 N. Michigan Ave.
Chicago, IL 60611
(312) 280-2750

Featured Partners

Book A Trip