There is nothing quite like summertime in Chicago y’all! Tyler & I have been taking little roadtrips to the windy city since we first started dating (it’s only a 6 hour drive from Lexington btw!), and it’s one of our favorite places for a weekend getaway. We’ve ventured in the winter & summer in years past, but summertime is the best time for a trip to the Windy City. We decided to make a last minute anniversary trip to Chicago a few weeks ago, and I’m so glad we did! We look full advantage of the beautiful summer weather. We did new (to us) activities, tried new restaurants & stayed in a totally different area than we normally do.
Summertime Chicago | What to do
Catch a Cubs game!
This one is kind of an obvious one, but don’t skip out on a game at Wrigley Field! We caught a day game, and the weather was so good! We headed up to Wrigleyville a few hours before the game to grab some tacos & beer at Bigstar Taco. The queso & atmosphere were so good. The area right around the field has been developed so much over the years, there are so many restaurants & bars to try out right around the field.
Even if you’re not a baseball fan, there is just something so fun about being in the crowd for such a fun sporting event. Grab a Chicago dog and beer & cheer for the cubbies.
Chicago’s First Lady Architectural Cruise
This is something Tyler & I have always wanted to do, and I am so glad we finally did it! It was such a fun way to spend a few hours. Our guide was amazing, and it was so interesting learning all of history & details of Chicago’s architecture.
We had a great experience with Chicago’s First Lady. I know there are several companies that do similar river cruises, but this one came the most highly recommended. We did a 11:30am time slot & the shadows were in our favor as far as photos go. We’re dying to go back for a sunset cruise.
I’m going more in depth on this down below.
Summertime Chicago | Where to Stay
When researching for this trip we knew we wanted to stay in an area we normally don’t. There are so many cool neighborhoods in Chicago, so we just wanted to switch it up a bit. We’ve stayed on Michigan Ave, downtown & in the Theatre District in years past, but the Fulton Market District might be my new favorite area.
This little neighborhood in Chicago is so cool y’all! It is FULL of incredible restaurants, and The Hoxton hotel. This hotel is pretty new to the city, but it is already gaining popularity. And for good reason! This hotel has the coolest rooftop pool area, yes a rooftop pool!, attached to Cabra. Cabra is the cutest, Instagram worthy restaurant with the yummiest frozen pisco sour.
While we loved our stay here, and thoroughly enjoyed the amenities. Not staying at the hotel? You can still enjoy the pool & restaurants. After 11am the pool is open to the public, and such a fun little slice of summer heaven. The first day we got there we spent some time by the pool, and it was such a relaxing way to spend a Chicago day.
Summertime Chicago | Where to Eat
This Peruvian inspired restaurant by Chef Stephanie Izard (the crazy popular chef behind Girl & the Goat) is such a fun spot. Spoiler alert– Tyler is a picky eater, so we just had apps & drinks here, but it is worth a visit! The queso dip was delicious and we had one too many frozen pisco drinks! This rooftop restaurant connects to The Hoxton pool, and can make for a super fun dining experience.
Another Stephanie Izard restaurant right around the corner from our hotel. We grabbed breakfast here one morning because we had a late lunch reservation, and it was delicious. Leave your diet behind & order the cinnamon roll, you won’t regret it.
They also serve lunch & dinner!
We grabbed lunch here before the Cubs game. Gimme all the tacos & chips. It was a great place to have lunch before the game. The open air restaurant looks right over Wrigley Field.
While this doesn’t scream a summer must visit, if you’re like us & have some special things to celebrate in the summer this is a great option. This steak house came HIGHLY recommended. I was a little apprehensive, but thought we would give it a go & I am so glad we did.
Between the food, the service & the ambiance, you will not be disappointed!
We only grabbed a drink here before dinner one night, but it had the best rooftop patio & atmosphere. The drinks were so good too. I was dying to try some apps, but didn’t want to ruin our appetite before dinner. Next time we definitely will though.
Y’all this place was SO good & so cute! The atmosphere was great, and the food was even better. We honestly weren’t that hungry, so we split two apps (the meatballs & ricotta pillows) and they were so delicious.
I stumbled upon this spot on Instagram, and immediately tried to make a reservation. Y’all this was weeks before we left & there were barely any openings. I kept checking back & was able to grab a late lunch reservation & I am so glad I did. This adorable restaurant is right on the river, and has the cutest decor. It transported me back to Italy. The pizza & salad we ordered were so yummy too.
Also known to have the best burger in town. We got in early-mid afternoon and hadn’t had lunch yet, so we needed a snack. Because we had a late dinner reservation and were staying around the corner we decided to see what all the hype was about. Tyler & I split the burger & fries and HOLY COW. It lives up to the hype y’all!
Little Goat Diner 
Aba
BIGSTAR TACO / Wrigleyville 
Pizzeria Portofino
Seriously looks and sounds like y’all had the best trip! SO many yummy eats!
xo Laura Leigh
http://www.louellareese.com