Chicago: Travel Guide

HIYA PEEPS!! I took one of my favorite trips ever back in 2019 to Chicago, but never shared the deets with yinz! With baseball season being back, I thought what a time to share my Chicago trip because the Pirates vs. Cubs game was a huge part of why I went!

Myself along with three other ladies decided to take a long weekend getaway to Chicago during a weekend the Pirates would be playing at Wrigley field so we could get to see a game at Wrigley field. The dates ended up falling Friday-Sunday in July. We knew Chicago had so many fun attractions and we had tickets to the game so we wanted to maximize the fun with a jam packed itinerary! We arrived Friday afternoon and headed to the Chicago Famous Lou Malnati’s for some classic deep dish pizza. It is HEAVY so prepare yourself. We ordered the Malnati Chicago Classic and a salad, because like I said it’s HEAVY. Def a fork and knife meal but it was so yummy. I don’t recommend taking leftovers because it didn’t reheat well.

Gelato dessert from Quartino

Next up was to check in to the hotel and head to Shedd Aquarium. We stayed at the Fairfield Inn & Suites Chicago Downtown/River North which was the PERFECT location. Walkable to the Riverwalk, Cloudgate (the Bean), Lou Malnati’s, and Magnificent Mile made this hotel perfect. We bought the Shedd tickets at the aquarium, however we contemplated purchasing through the Chicago CityPass. The CityPass is $109 for adults and $89 for kids ages 3-11. It includes the Shedd Aquarium, Skydeck, Field Museum, and two more attractions of your choice out of four offered. We weren’t going to get the best use out of it because a whole afternoon was blocked off for the Pirates game.

Cosmo from the Signature Lounge at the 96th Floor

After spending a couple hours at Shedd, we headed to the hotel to refresh and get ready for dinner. Our reservations were at Quartino, an Italian restaurant. The dining area was a large open room with several tables scattered around the floor. My sister and I split the calamari and the clam linguine with white wine sauce. For dessert we split the gelato. Everything was WONDERFUL.

For a night cap, we went to the Signature Lounge at the 96th floor of the John Hancock Building. The sights of the city are stunning from here. The cocktail list is classy and perfect for sipping while taking in the gorgeous views. Make a reservation if possible because this spot can get busy, however they try to keep it very spaced out and intimate so there will likely be a wait.

The next morning I headed on a quick run down the Riverwalk. There’s no better way to see a city than like a local on a morning run. Afterwards, we all headed to Brunch, a breakfast spot. With a name like Brunch you gotta be expecting some BOMB food and they did not disappoint. We had reservations here as well. Ya gotta have sweet and savory so we ordered donut holes and then the best breakfast sandwich ever. Unfortunately, since my trip this restaurant has closed 😦

To the game we went!!!! Tickets for Wrigley were definitely pricey compared to PNC Park duh. If you don’t want to spring for the Wrigley tickets, you can always watch the game from one of the surrounding rooftops filled with bleachers! The appeal of Wrigley Field is the history, but tbh PNC Park will forever be my favorite park and view. In classic Chicago fashion, I had to get a Chicago dog topped with all the fix-ins! The Pirates lost, but hey we still had a great time.

A quick nap was warranted after our big afternoon. After the nap we went to the SkyDeck for pics of course. You only get a minute to take pics so plan your poses!! You can pay more to skip the line, but we decided to wait. You can buy the digital package for a flat fee which is what we did. It ended up being $40 for the package we selected, so only $10 per person. We headed to Hampton Social for dinner and drinks, then called it a night.

Our last day in the city began with walking from our hotel down to the Bean in Millennium Park. We stopped on the way at Stan’s Donuts for a sweet treat to start the morning. We took all the pics at the Bean and headed to our last destination, Eataly. This fun Italian market was a great way to get a little taste of everything Italy. We bought the Eataly Passport for $28 which allowed us to taste wines, gelato, truffles, fresh pasta, and focaccia. They are always having events, classes and specials at Eataly so be sure to look out for those when planning your visit! We also snagged some pasta to bring home for our family of Italians.

Mid-afternoon we headed to the airport and flew home to the Burgh. Our trip was wonderful and truly gave us an amazing look at the “Windy City.” When I plan trips people think I overdo it with the itinerary, but truthfully this city was so full of experiences that we needed an itinerary to fit it all in. My detailed itinerary is below if you’re interested when planning your trip!

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