Recently, my twin sister and I took a last-minute mid-week trip to Chicago (WHY. NOT. RIGHT?). Neither of us had ever been there before so we were determined to cram a lot in. I feel we achieved this. This is how:

Tuesday:

7:30am: Arrive at Billy Bishop Airport. Impressed by convenience of location. Not impressed by stupidity of tiny baby ferry journey. Having been told that Porter’s lounge area provides free drinks and food, grab turkey wrap. “That’ll be $11 please, miss.” Quietly return turkey wrap. Pocket several almond snackpacks.

9:45am: Flight lands at Chicago’s Midway Airport. Airport smells distinctly of popcorn. We are not mad about it.

11:00am: Check into the Drake hotel. Are greeted by this v. chill sign:

12:00pm: Shop til we drop on Michigan Ave., aka “the Magnificent Mile.” Local Topshop employee throws massive shade on Toronto’s Topshop—”It’s barely anything, literally why even bother.” He’s not wrong.

2:30pm: Consume the largest salads in human history from a bakery chain I forget the name of.

7:00pm: Get drunk by accident in a Chipotle over steak salads. Try on each other’s rings for some reason? Sisters.

8:00pm: Take in a show at The Second City. Much bourbon, many laughs, very satire.

11:30pm: CVS sells premixed margaritas you can buy any time of night. We abscond to the hotel room with several, and watch late night local TV. Make plans to wake up early and take on Chicago.

Wednesday:

10:30am: Whoops. Wake up, coffee up, head out.

11:30am: Have been walking for too long in search of The Bean. On some kind of pier. Not mad, the pier is great too—there’s a ferris wheel and food stalls and the lake is gorgeous.

12:00pm: Finally make it to Millennium Park. Take a hundred selfies in The Bean, check the cray fountains, and generally marvel at the mixture of waterfront, giant, sculptural art, and beautiful high-rise architecture. Nice work, Chicago.

2:00pm: Arrive at Wrigley Field, ready to figure out what baseball’s whole deal is, only to discover the game is sold out. Mid-week! Two kind employees of the field come over to console us, and give us FREE TICKETS in celebration of the ballpark’s 100th birthday! We shiver and cheer and eat hot dogs as the Cubs gain a 5-7 lead only to lose by 3 runs in the 9th. Classic Cubs.

6:00pm: Deep. Dish. Giordano’s is recommended by basically everyone on Yelp, and a pleasant 10 minute walk from the stadium. We share a small pie between us and leave feeling like we’ve eaten two XLs alone. It had to be done.

8:00pm: A free (!) show at the famous iO improv theatre. All-girl troupe Virgin Daiquiri (alums include SNL’s Aidy Bryant and Cecily Strong) blow the house down.

10:30pm: We’re 100 years old and “feel tired from a big day.” We get back on the Loop and head to the hotel for a snooze and some Night Chips.

Thursday: 

9:30am: Awake, showers, coffee, Chobani.

11:00am: Boat tour by the Chicago Architecture Foundation. Kindly volunteer tour guide named Val tells secondhand jokes about the time David Letterman took the tour ten years ago amidst facts about the city’s stunning buildings.

12:30pm: Decide to splurge on lunch at the ritzy Ralph Lauren Restaurant, which looks like something out of Mad Men. Sip wine in front of a personal fireplace while two socialites gossip about how someone’s uncle ruined the cotillion.

2:00pm: Drunk visit to the Art Institute. It is none the less gorgeous for our lunch-boozy state. Art, artefacts, gift shop, repeat.

7:00pm: Naptime.

12:00am: After sushi and a walk around the closed shops of Michigan Avenue, head to the 95th floor of the John Hancock building for a nightcap overlooking the city. The drinks are meh and it looks kind of like a tired Swiss Chalet in there, but that VIEW.

1:30am: Head to bed for a flight in the morning, already planning a trip back.