The Long Weekend: Chicago

Jon and I often discuss where we might move next. This year we had the opportunity to move to New York City. It wasn’t the right time for us as we just made Austin our new home. And Jon is a Texas boy at heart. So obviously it shocked me when he said we could move to Chicago in the future after spending a few days there in August.  The beautiful summer weather tricked him into thinking snow wouldn’t be so bad. Plus, we had a ball hanging out with our friends all weekend.

Five Days in Chicago Itinerary:

Day 1: Land at 10:30, check into the hotel, drink a beer, go to the Cubs game. We vacation hard. Dinner and drinks at Parson’s Chicken & Fish.

Day 2: Be lazy, Brunch at a place called Brunch. Delicious. Walk around River North and Lincoln Park. Go to random person’s surprise party at Fatpour Tap Works, then play old school games like Frogger at the Emporium Arcade. Close down the bars at 10:15 ;). Get amazing drunk food at Cheesies Pub & Grill. Yes, it is a grilled cheese place. Yes, I did order mac & cheese on my grilled cheese.

Day 3: Visit coffee shops in Wicker Park area and West Loop. We really enjoyed the atmosphere at Sawada coffee. Very unique. eat deep dish pizza at Lou Malnati’s. Go to Eataly. Immediately regret the decision because we were stuffed from our pizza and it was pricey.

Day 4: Chicago Bagel Authority – meh. Art Institute of Chicago – famous for their collection of Impressionist art. Be sure to check out Georges Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic and Pablo Picasso’s The Old Guitarist – my favorite piece I’ve seen by Picasso. Definitely prioritize because the museum is huge. Portillo’s for lunch. White Sox game. We were rained on for the first time at an MLB game. Sweet  Mandy B’s for dessert.

Day 5: Be lazy. See the Bean. Walk around the park. Go to the FREE zoo in Lincoln Park. Give the kids who knock on the glass dirty looks. Fly home.

Things I would do differently:

• Skip Portillo’s. I know I’m going to get some hate for this, but hear me out. Portillo’s is like the Whataburger of Texas. If you are a Texan, you swear Whataburger has the best burger. Out of towners don’t seem to get it. It’s the same for Portillo’s.
• Skip the Bean unless you like to see people staring at themselves in a shiny object. In that case, this is the place for you.
• Make it a three-day trip. We had a blast hanging out with friends, but if you are going just to see the sights. I think you could make Chicago a three-day weekend trip.

Favorite parts of the Trip:

• Seeing friends we hadn’t seen in a few years.
• Wrigley Field – At 1:20 on a Friday, the stadium was packed, the people were friendly. We bought tickets on Stubhub for a little bit cheaper than the box office. The area around Wrigley is awesome. Lots of bars, people hanging out. Downside is trying to get on the train after the game ended. Pro tip: Walk to the next L station. This was stadium #6 on tour de baseball stadiums.
• The L – I was told you don’t call it the metro in Chicago. I’m not sure this count as favorite, but I love a city with a functional public transportation system. You can train from the O’Hare into the city. We bought a seven-day pass for $33, which included the $5 trip from the airport.
• The White Sox’s stadium – definitely not as neat as Wrigley Field, but we had awesome seats. Stadium #7.
• Emporium Arcade – Because I could play Frogger all day every day.