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Romantic Summer Weekend in Chicago

Chicago, IL, United States
3 Kudos
Decided to make a weekend trip to Chicago, as it's long been on my travel bucket list for the food and the wide array of entertainment. Fortuitously, our trip also happened to coincide with the Air & Water Show and the solar eclipse, and we were thrilled to experience both during our getaway.

We arrived early on a Saturday morning and made the easy trip from O'Hare to our hotel downtown. After checking in, we made our first pit stop at Rick Bayless' famed mexican eatery, Frontera Grill, to grab some delicious brunch.

Afterwards, we trekked up to historic Wrigley to catch an afternoon Cubs game. To our surprise, around the 3rd or 4th inning, we heard and saw fighter jets whiz around the city from our seats in the stadium, and for the next few innings, I think more people were on the lookout for the squadron of Blue Angels rather than paying attention to what was happening on the field.

After a memorable experience at Wrigley (for completely unexpected reasons), my girlfriend and I returned to River North to experience Chicago deep dish for the first time. Unfortunately for us, throngs of tourists had the same idea, and rather than wait an hour-plus for dinner, we wandered north to hit up Portillo's for their hot dogs and beef sandwiches. A solid alternative with a fraction of the wait.

We wound down the night with a leisurely, and romantic fireworks cruise through the Chicago river, the Locks, and onto Lake Michigan. Every Saturday in the summer, the city of Chicago puts on a spectacular fireworks show, and we were more than happy to take it in from the deck of our tour boat.

The following day, we kicked off our morning by journeying to the top of the Willis Tower to take the obligatory photos on the glass-bottom floors a hundred stories up from the ground. Once we finished, we made our second attempt to sample deep dish pizza, this time successfully scoring a table at Lou Malnati's. It was tasty and filling, but still can't compare to a NY style slice.

In the afternoon, we bused up to Lincoln Park to watch the Blue Angels again, this time without the distraction of a baseball game, and hung around the neighborhood at the free zoo and conservator. We grabbed a light dinner nearby before catching a show from the Second City. It was a fun night, although I still prefer the NYC comedy scene.

We spent most of our last full day in Chicago in Grant Park, where we hit up the Adler Planetarium and Field Museum, while also periodically looking upwards to experience the eclipse thanks to the free sunglasses we received at the planetarium. As the day wound down, we made our way west to grab try the highly-acclaimed burgers at Au Cheval, before calling it a night and pretty much wrapping up our Chicago weekend getaway.
Story Details


The Second City
Famous improv comedy troupe; acts may be politically, sexually, and many other sorts of offensive, but that's part of the fun.
Lincoln Park Zoo
Free zoo in the heart of Lincoln Park, although not at expansive as most other major zoos

Points of interest

Grant Park
Expansive waterfront park where you can find a number of museums, Soldier field, and numerous paved walking paths
Willis Tower Skydeck
Willis Tower Skydeck
Climb one hundred plus floors to get unparalleled views of Chicago, and experience the thrill of having nothing but glass between you and the ground


quick-service outpost from Rick Bayless specializing in tortas and churros
Lou Malnati's Pizzeria
Lou Malnati's Pizzeria
Renowned for their deep dish pizzas, but be weary of long lines
Portillo's Hot Dogs
Carnival-like atmosphere where you can try Chicago style hot dogs, polish sausages or beef sandwiches
Frontera Grill
Famed Mexican restaurant from Rick Bayless, with brunch, lunch and dinner offerings.


Wrigley (via Kennedy)
Wrigley (via Kennedy)
Famed home of the Cubs, a historic park a short journey north of downtown Chicago

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