Travel  /  

Apr 09, 2019

Our Travel Guide for A Weekend in Chicago, IL

We recently took our travels to the “windy city” and it definitely lived up to its name. Not going to lie, we were a little intimidated by the weather forecast (being from sunny Southern California) and we were ready to put our layers to the test! Turns out, Chi-town is not only beautiful, but the midwestern charm felt throughout this city was just enough to warm us up. Home to renowned museums, eclectic neighborhoods, exhilarating sports, and upscale boutiques, we couldn’t wait to explore. With 48 hours in this bustling city, we gathered the highlights of our lovely weekend in Chicago to share the getaway with you here! Keep reading for where to stay, what to do, and where to eat in Chicago! *Deep-dish pizza sold separately* 

Weekend in Chicago, Things to do in Chicago

Where to Stay

Weekend in Chicago, Things to do in Chicago

Ritz Carlton Chicago: For our first time traveling to the windy city, we were truly lucky to stay at the Ritz Carlton Chicago. The Ritz and luxury lodging really do go hand in hand. From the artwork to the interior design and the amazing hospitality, this hotel lived up to its reputation and then some! The lobby is located on the 12th floor and when you exit the elevator you are greeted by a magical lounge area complete with a beautiful floating installation from the ceiling. The stunning hotel underwent a huge renovation about a year and a half ago, so everything has a modern, elevated touch. Being just a short walk away from Michigan Avenue’s shopping & attractions, guests can step outside and enjoy all of Chicago’s surrounding beauty. 

Weekend in Chicago, Things to do in Chicago

Where to Eat

Weekend in Chicago, Things to do in Chicago
3 Arts Club Cafe at Restoration Hardware

Torali Italian-Steak: Lucky for us, we didn’t need to venture out of our hotel for this fine dining experience. This steakhouse is modern in approach and Italian in spirit. The food definitely took our taste buds on a magical adventure, from the “Risotto di Fungi” to the market special “Surf & Turf” we were in absolute heaven! The meal wouldn’t be complete without a lovely wine pairing that was right up our alley. The restaurant staff was so great and had so much insight into the dishes and inspiration. We highly recommend dinner her for a mouthwatering dining experience. 

Weekend in Chicago, Things to do in Chicago Weekend in Chicago, Things to do in Chicago

3 Arts Club Cafe at Restoration Hardware: We were thrilled with anticipation when we added this cafe and store to our agenda. Not only do we want to furnish our dream home head to toe with Restoration Hardware, but we couldn’t wait to dine at the 3 Arts Club Cafe which had the best ambiance we have ever experienced. While we were waiting to be seated, we grabbed a mimosa and explored the many floors of Restoration Hardware, essentially decorating our dream home, which truly made the wait not so bad ;). We were lucky enough to dine in the Grand Courtyard, which had an atrium that let in the most beautiful natural light accompanied by a fountain in the center lined with Heritage olive trees. Oh, and did we mention the food?! It was phenomenal! We enjoyed a warm latte at the end and really just took in the beautiful atmosphere. 

Weekend in Chicago, Things to do in Chicago

The Hampton Social: When someone suggests happy hour, we always say “Yes way rosé!” This adorable nautical spot located in River North had both a delicious rosé selection and delectable brunch options. Aside from snapping the infamous shot of the “Rosé all day” sign (we had to!) and soaking in the east coast waterside vibe, this trendy joint is great for listening to live music & catching up with your closest friends. *Note the drinks taste as good as they look* 

Weekend in Chicago, Things to do in Chicago

The Original Maggiano’s Little Italy: Maggiano’s is the best restaurant for that classic Italian feel, and we knew we had to make a pit stop here when we found out this is where Maggiano’s came to be in 1991! Eating here is never a disappointment, but the overall ambiance in the original location was like no other. If you want that homey & cozy feeling while you chow down on chicken parm, this is the place!

What to Do

Weekend in Chicago, Things to do in Chicago

The Bean: Word on the street is that this popular landmark is called Cloud Gate, but ask any Chicagoan and they will call it “The Bean”. You can’t leave this city without stopping to see one of Chicago’s most prominent features. Makes for the perfect photo op at any angle! 

Weekend in Chicago, Things to do in Chicago

Skydeck: Now honesty really is the best policy… so we have to share our experience at Skydeck with you all. We were sooo excited to take Chicago to new heights and see the beautiful city in all its glory. Unfortunately, we happened to go on a day where the weather conditions were extremely poor. We decided to be optimistic since we already purchased tickets but when we arrived at the top, it is with great sadness that we report we were unable to see anything (lol)! Zero visibility is an understatement. We still managed to have a great time, but we recommend going on a day where the weather is relatively clear. Looks like we will have to go back and give it another try in the future. 

Ritz Carlton Spa: Between traveling and chilling winds, your skin will probably be in desperate need of some hydration! This was the ideal oasis to escape from the city’s volume for a bit and have hydrating facials, rejuvenating pedicures, and a moment of relaxation. 

Weekend in Chicago, Things to do in Chicago Weekend in Chicago, Things to do in Chicago Weekend in Chicago, Things to do in Chicago

Museum of Contemporary Art Chicago: This museum was within walking distance from our hotel, so we had plenty of time to head over and check it out. Located in downtown Chicago, the museum was established in 1967 and is one of the world’s largest contemporary art venues. We had so much fun learning and exploring this beautiful museum. If you have some extra time before you head to the airport, we suggest checking it out!

Weekend in Chicago, Things to do in Chicago Weekend in Chicago, Things to do in Chicago

Where are your favorite places to go and things to do on a weekend in Chicago?

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