My Favorite Chicago Hotel + Weekend Recap

I spent Labor Day Weekend in Chicago with Conner, my family, and some of our best friends and we’re back in NYC right now still reminiscing on how awesome the trip was. We flew in early Friday morning and started LDW off with boating on Lake Michigan on a beautiful 42’ sailboat. I know I’ve said it before, but renting a boat in Chicago and parking out in the Lake Michigan Play Pen is one of my all-time favorite Chicago experience. In the past I’ve always rented boats (with a captain) through Boatsetter. It’s available in most big cities and you can use my code OLIVIA10 for 10% off your next trip 🙂

The Langham Hotel

I’ve stayed a good amount of the luxury hotels in downtown Chicago, but have to say, nothing quite beats The Langham Hotel. My stay over the last few days completely made the weekend – and also made leaving yesterday so hard! Everything from the prime downtown location, exceptional service, timeless glamour, culinary experience, and signature pink touches made the weekend unforgettable. Here are some pictures from inside the suite…

Pink Silk Tank (xxs) | Satin Pants (xxs, short)

Possibly my favorite part about the entire experience of staying at The Langham was the club level on the 12th floor. Every morning on the 12th floor there is a fabulous breakfast buffet with a coffee bar, study area, fireplace, and floor to ceiling window views of the Chicago River. That and the waterfall shower…hard to top!!

The hotel’s restaurant, Travelle, just launched picnic baskets for guests to enjoy outside the restaurant throughout the summer. So whether you’re dining al fresco along the Chicago River, catching a movie at Millennium Park, or exploring elsewhere in the city, these picnic baskets include everything needed for enjoying the warm weather. With three different options to choose from, each basket provides the perfect combination (such a cute date idea!). The picnic baskets couldn’t have been more perfect for our day out on the sailboat. Travelle had the baskets all packed up for us with gourmet sandwiches, salads, spreads, breads, fruit – and even caviar! They also include alcoholic pairings. For more information about the picnic baskets, go here. The Langham is also home to Chicago’s first and only Forbes Travel Guide Rated Five-Star Spa & Health Club. They are currently offering 2 unique tiers of memberships: the Luxury Horizon Membership + Signature Membership. For more information about their spa memberships, go here.

On Saturday my parents drove into town from South Bend to join us in celebrating my older brother Austin’s 30th birthday. We had bottomless brunch at The Bandit, a delicious dinner at one of my favorite Mexican spots, Barrio, and finally got to see Hamilton!  All I have to say is if you haven’t seen it yet, you need to find an open weekend and get tickets..it definitely lived up to all the hype.

Leopard Print Dress (wearing xxs petite)

Sunday we attended the wedding of our good friends Madison and Seth at The Drake Hotel. If you saw snaps from the night on my story, you saw how beautiful it was! Everything from the thousands of bright red roses to Madison in her sparkling ball gown was like a fairytale. Such a beautiful night with so many of our best friends!

Bronze One Shoulder Gown (xxs) | Shoes | Bag | Earrings

Later this week I’ll be posting an updated version of my Chicago City Guide with some of my new favorite places  I’ve discovered since I left the city. Thankful for another great weekend in the Windy City…until next time Chicago 🙂