Travel

46 hours in Chicago

Here’s a Deep Dish on how I spent my weekend on my first-ever trip to Chicago. I don’t know how I slept on this town for so long.

I am not an ambitious see-everything-on-the-list traveler so my itinerary is never aggressive. I like to walk the city and have a lot of flexibility which means I only plan a couple time-sensitive activities each day. I loved how the city felt busy and bustling but not in a stressful, hurried way.

FRIDAY

Traveling with my daughter and her roommate, we took a direct 2.5 hour flight on Southwest from Jacksonville (JAX) to Chicago Midway (MDW), arriving at 7:30PM.

We politely refused a ride from a driver only to make our way towards the taxi stand and have someone call him over to take us to our hotel. Awkward. Thirty minutes later, we checked into our rooms at Virgin Hotels Chicago.

You guys, how do I invite my friends over to get ready with me without it being weird? Hanging out in the girls’ room, I loved seeing their hair and makeup mirror time. We had a fast turnaround in order to head to London House at 9PM to meet a friend. I’m not a selfie taker and hate to ask strangers to take my photo but, thank goodness we did. Check out this rooftop view!

The evening went on to involve typical night-out things. We ended with a french-fry-centric midnight dinner at Elephant & Castle, a pub by the hotel.

SATURDAY

Our first activity of the day was an 11:30AM Walking Food Tour. We noshed on:

Deep Dish Pizza at Lou Malnati’s Pizzeria
Cheddar/Caramel popcorn at Garrett’s Popcorn Shop
Hotdogs at Jimmy’s Gyros & Grill
Italian Beef Sandwich at Exchequer Restaurant & Pub
Brownies at Palmer House Hotel

Hotdog with pickle spear? Hotdogs are weird enough.

Palmer House is gorg. The brownie looks like brownie.

We continued the walking tour through Millennium Park, enjoying the shiny Cloud Gate sculpture known as “the bean” and river views.

After the tour, we planned to go to the Christmas Markets but changed our minds after seeing the long line. The young ones went roaming on their own while I met up with friends at The Gage.

Yay, friends!

Which brings us to the whole reason we are in Chicago. I planned this trip around tickets to see Cake. Our evening was consumed by trying to walk far enough get an uber to The Salt Shed while a parade closed off big chunks of the city.

SUNDAY

After bagels and coffee at the hotel and a brisk 10 minute walk, we lined up at The Art Institute to get in as soon as it opened at 11. The two art majors immediately parted ways and went chasing favorites.

We only had 45 minutes (in a half day museum) but it was still nice to get a little sip of it before heading to the airport.