Gourmet Getaways

48 hours in Chicago: A perfect girlfriends' getaway

Chicago happens to be in my top three all-time favourite American cities: The architecture! The food! The galleries! The shopping! The spas! Here’s how to spend two perfect days in the city

Do-rite donuts

Do-rite donuts

Chicago happens to be in my top three all-time favourite American cities: The architecture! The food! The galleries! The shopping! The spas! A few of my best buds from university are now sprinkled across the country so we decided to meet in Chi-town for a weekend of full-on fun. Here’s how to spend two decadent days in Chicago:

Day 1

If you can, fly Porter Air, for a quick trip like this, it got me from downtown Toronto to Chicago in a jiffy, where a train ticket from Midway Airport to our downtown hotel took under a half hour and cost just $2.75. (Plus, there’s the free onboard wine in real glasses during the short flight.)

Once you land, fuel up on coffee at Intelligentsia and then some over-the-top donuts from Do-Rite. Now you’re truly ready to begin the weekend festivities!

We got a deal, did the math, and it turned out if the four of us stayed in one room with a pullout couch, we’d save big-time on hotel costs. So, we happily checked into the 5-star, 5-diamond Peninsula Chicago.


Peninsula Chicago

A highlight of the trip was catching up over their famous Afternoon Tea in the sun-dappled Lobby, “It reminds me of the imaginary tea parties I had as a child, except that it’s real and I’m grown up,” said my friend Shragit. But I also loved my morning swim and coffee in the hotel’s lap pool, which was like a crow’s nest overlooking the city. Tamara said the swim inspired her to start our first full day in the city. An architecture boat tour on the river in this architecturally significant town is a must, (even though it was freeeezing out and we almost died).

But don’t worry about us; we warmed up over a few hours of intense shopping, and then enjoyed dinner at GT & Oyster, shared plates of everything seafood and delicious!

Day 2

We hopped on the very easy to navigate Chicago transit and took the train to the hot West Loop area for brunch at Little Goat, a new offshoot of James Beard award-winning chef Stephanie Izard’s Girl and the Goat. I had the Fat Elvis Waffles, which were hot, fluffy, bacony, bananay and peanut-buttery, but above all, yummy.


Fat Elvis Waffles

And then, as I should have expected, the rest of the day was a shopping blitz of Neiman-Marcus, Bloomingdales, Sak’s and the rest. A shopping tip from Jacki: “If you go loose on top go tight on the bottom, if you go loose on the bottom go tight on top.” Pit stops at Millennium Park and the Art Institute of Chicago made for a little infusion of culture.


Millennium Square, Chicago

We stayed the second night at the Fairmont Chicago, which is modern, centrally located and has gracious, helpful staff. They’ve also got a great steam room and relaxation room setup in the spa, and we took full advantage by relaxing for an hour before dinner.

Our final stop was dinner at Embeya, an Asian-spin restaurant with a great vibe and delicious small plates for sharing (I can particularly recommend all the veggie sides). Our waitress was so happy to see good friends enjoying a weekend in her city that she sent over sherry after dinner, and we toasted each other — and Chicago.