At the beginning of the month, my friends and I took a road trip to Chicago for the Fourth of July, and it was such a fun place to spend the holiday weekend! Chicago will always be one of my favorite cities, and it makes for the perfect weekend road trip. I definitely have some city girl in me, but also love being on the water, so being able to get a taste of the city life, while also spending time on the lake makes my heart happy! Now that I have been back to the city a few times, I wanted to share a few of my top favorite spots in Chicago that I know you would love, too!
I wanted to start off with where we stayed, because location is definitely important in the city! I had the pleasure of staying at the Loews Chicago Downtown Hotel, and I couldn’t have asked for a better place to call home for the weekend! It was so luxurious and comfortable, everyone was very friendly, and the location was perfection. Just outside our window, we had beautiful views of the city and the Riverwalk. There is nothing I love more than the city skyline lit up at night. I’ve decided that the beds in our room just might be one of the most comfortable beds I’ve ever slept in during all of my travels! There was a Starbucks down in the lobby, which was perfect for grabbing something on-the-go, or a morning coffee. There is an indoor pool if you want to go for a dip, and I was so impressed by the gym (there’s even two Peloton bikes!) My dog Ruby wasn’t traveling with me, but she sure would’ve loved it if she had been! I wanted to be sure to mention that the hotel is very pet-friendly which can be hard to find while traveling, and even offers a gourmet menu for dogs and cats, special bedding, pet-walking and other amenities for your pets! We were just a 10 minute walk to the Navy Pier as well as Magnificent Mile shopping, a few steps away from the Riverwalk, and we were able to walk to many of my favorite restaurants that I listed below! *Back in May I stayed at the Loews Sapphire Falls Resort when we visited Universal Orlando (see post here), and our stay there was just as magical! I can’t recommend Loews Hotels enough, and I am so excited that they will have a new location opening here in Kansas City next year!
The hotel had great dining options, with the ETA Restaurant + Bar, as well as Streeterville Social, their outdoor rooftop lounge! We ate at Streeterville Social, and it had the most beautiful rooftop views! The food was delicious, and the cocktails were SO good. It’s the perfect spot to spend a summer evening and grab a drink with friends, or stop by for brunch with a view. I definitely recommend trying the drink ‘Rosy Cheeks’!
Favorite Places to Eat:
Summer House Santa Monica- This is hands down my favorite spot to go every time we visit Chicago! There is just something about the atmosphere and vibe of the place! It’s soo cute inside, and everything is very light and airy. It feels like the ocean should be right outside! The food is absolutely delicious, and they also have a some really yummy baked goods at the front when you walk in. I am very picky about my guac and I feel like restaurants just don’t often make it well, and their’s is some of the best I’ve ever had, so make sure to order it! This is the perfect spot to grab your friends and head here for dinner and drinks, or even brunch, and just sit back and enjoy the laid-back vibes. I definitely recommend making reservations a few days ahead of time.
Quartino Ristorante- Some of the best Italian food! I also really love the atmosphere of this place, too..it’s so fun! Their dishes are meant to be shared and come in reasonable portions, which I liked because often times Italian restaurants just make their dishes SO huge. They also bring the food out as each dish is ready, and not all at once, just like in Italy! Get it while it’s hot! Both the pizza and the pasta were to-die-for.
Wildberry Pancakes & Cafe- Our FAV breakfast spot. We went 3 times this past trip, and twice the trip before that, ha! They offer a classic breakfast, which is my personal favorite. I don’t usually prefer a fancy breakfast, or anything too trendy. Their pancakes are SO good, they literally melt in your mouth. My friends and I are constantly talking about them! This place gets VERY busy, but luckily they move very quickly. Tip: get in line via the Yelp app! You can pick which location you want to go to (we always go to the 196 E Pearson St. location), and you can get in line, and you can then keep track of what number in line you are, and it will text you when you have 5 minutes to get to the restaurant and check in! So helpful and such a time saver.
The Hampton Social- yet another spot that is incredibly cute and photo-worthy, and the food is delicious as well! Being from the East Coast, I love the overall vibe of the restaurant as it really does feel as though I’m back on the Coast! This is such a fun place to go with your friends, and if you go for dinner/drinks, be sure to order one of the giant seashell drinks for the table! We went to the River North location and it was so pretty inside, and we took a photo by the iconic ‘Rose All Day’ neon sign that’s on the green ivy wall. I’m sure you’ve seen it all over Insta! The Streeterville location looks soo cute too, and has a beautiful rooftop patio! Both locations have the perfect vibe for brunch, and definitely some cute ‘grams and stories to go with! I recommend making reservations!
Garrett Popcorn- this is Chicago’s famous popcorn! It is so, so good and if you love popcorn, I definitely recommend making a stop here! Often times it’s busy, so you might have to wait in line for a little, but it’s worth it!
Places to Go:
Navy Pier- this one is a given! You can’t go to Chicago without spending some time at the Navy Pier. Like I mentioned above, I love that you can spend some time on the water while staying in the city. The lake is so big it literally looks like an ocean, which I love! You can head to the Pier and hop on a boat tour, ride the huge ferris wheel and other amusement rides, and grab a bite to eat…there’s so many yummy options to choose from! We considered renting a boat on the Fourth to spend the day out on the lake like many people do, but our plans ended up changing. That is always a fun option that you could book ahead, though! Memorial Day through Labor Day they have fireworks at the Pier every Wednesday and Saturday, and you can check the schedule for the rest of the year here, as well as info on their dinner cruises on the lake!
The Lake- tied in with going to the Navy Pier, you can also walk along the lakefront trail, or many people will also bike/run the trail, too! There are public beaches along the lake, some close to the Pier, where you can go to hang out and swim for the day!
Magnificent Mile- I am sure you may have heard of this famous stretch of shopping before! If you’re looking to go a little shopping while in the city, head here! There are so many stores, designer shops, department stores, and restaurants, too.
Millenium Park- this is where “the Bean” is located! If it’s your first time in Chicago, this is definitely a fun sight to go see, and spend the day in the area!
Riverwalk- this was just steps away from our hotel, and we had a view from our room! It’s a pretty area to spend the day by the water while grabbing a bite to eat, or just walk along the river! You can also take a boat ride, or even rent kayaks.
I hope you find this helpful if you’re planning a trip to Chicago, and I’d love to hear if you try any of these spots out! Please let me know if you have any questions at all! XO, Rachel
This post was in collaboration with Loews Chicago Downtown Hotel. All opinions are my own.
