I am a city girl through and through, so when I had the opportunity to go to Chicago for a few days to tag along with Jared while he was there for work I knew I had to do it. I had only been to Chicago once before and it was in the summer (see more details on that trip here) which I very quickly learned is a much different vibe than the middle of February. Nonetheless, I had a wonderful time. Here is an in-depth Chicago winter travel guide if you plan to visit the Windy City in the dead of winter.
Chicago Winter Travel Guide
The Details
We stayed at The Aloft River North, which was a stunning hotel in a great location. It wasn’t far from touristy things but also had some great local places not far too. It also had a delicious restaurant and coffee bar downstairs.
Itinerary
Saturday
Shopping at Michigan Ave
- Dylan’s Candy Bar: A must stop in Chicago and NY. This candy wonderland is actually owned by Ralph Lauren’s daughter and has every candy you can imagine.
- Ralph Lauren: This is one of the largest Ralph Lauren stores and at the top of Jared’s list. It’s a stunning store with remarkable merchandising. If you love fashion it’s inspiring to pop in.
- Ulta: I forgot my curling iron so we had to make a quick stop to grab a new one.
Lunch at Hampton Social
Hampton Social is one of my favorite restaurants. I had been before and fell in love with the Instagram-able atmosphere and the food is amazing as well. I highly suggest the Lobster Roll and Jar of Crab!
Nap
Since we had an early morning flight we were tuckered out and needed to rest for a little bit before we kept going.
This is of course is must do in Chicago. We planned to go right before sunset since we had a spot picked out nearby for pre-dinner drinks. It’s definitely a tourist stop but is something you have to do!
Chicago Athletic Association/Cindy’s Rooftop
This was somewhere new for us. One of Jared’s friends suggested it and it was the coolest place. It’s a multi-level hotel/restaurant. On the ground level, there is a Shake Shack, outdoor-inspired bar/casual dining and a coffee place all in different rooms/pockets of the hotel lobby. On the second level, there was a nicer restaurant and casual hangout with simple food and drinks. Then finally, on the rooftop, there was a swanky bar and restaurant. If you make reservations you can bypass the line but if you just want drinks the line is pretty long but goes by relatively quickly and is TOTALLY worth it. The menu is pretty selective and pricey so I would recommend just grabbing a drink there.
I found this gem on Pinterest and it was 100% everything I dreamed of and more. I would recommend getting a reservation on OpenTable to ensure you get in, but the atmosphere is very Restoration Hardware like with great food! Perfect for a nice romantic dinner.
Sunday
Bagels/ Coffee at Beatrix
I was really taking it easy and sleeping in Sunday morning, so I grabbed a bagel from a place on the same block and yummy honey cinnamon latte from the hotel coffee bar.
One of my favorite treat yourself moments is to get a blowout at Drybar. Since I had the time and a photoshoot it felt like a no brainer.
Photoshoot with Flytographer
I love doing photoshoots in new cities, so I booked a photographer through Flytographer and was able to sculpture tour the city and take photos along the way. See where we stopped below.
Use promo code ANGELA50 for $50 off your new photoshoot with Flytographer (ends 12/31/2020)
Merchandise Mart for Jared’s Event
I then met back up with Jared for a cocktail hour and dinner for buyers and vendors at market.
Monday
Room Service
Since I was in the treat yourself spirit I splurged with room service and The Beatrix has probably the best bacon I have ever tasted so it was worth it!
My photographer actually suggested visiting the Chicago Cultural Center and I am so glad I did. It was free and featured art from local artists and has in the most stunning building with the iconic Tiffany Dome.
“The magnificent translucent dome, 38 feet in diameter and made of Tiffany Favrile glass, is cut in the shape of fish scales. At the top of the dome are the signs of the zodiac. At the base of the dome is a quotation from the British author Joseph Addison. The dome glass, lighting fixtures, wall sconces and chandeliers were made by the Tiffany Glass and Decorating Company of New York. The supporting frame was constructed by the Chicago Ornamental Iron Company.”
Walked Around State Street
I walked around State Street for a little bit and popped into the nicest Target I’ve ever seen in this cool old historic building. I needed an umbrella but it was a nice surprise to see something so unique.
Lunch at Somerset
My blogger friend, Megan at Bowtiful Life, recommend this spot and it was quaint and absolutely my kind of vibe. It was the perfect lunch spot for one.
I had about an hour and a half before I had to meet Jared to go to the airport so I decided to go to aquarium, however, when I got there the line was way too long. Since it was President’s Day kids were out of school and free and Illinois residents were also free so there was no way I was going to have enough time.
Instead of the aquarium, I grabbed a donut before heading to the airport.
Downtown Sculpture Map
On My List But Got Cut
I had a few things I wanted to do but just couldn’t squeeze them.
Restaurants:
Things To Do:
What I Packed
I tried to pack “light” because I wanted to stick to a carryon. I kept everything to one color palette of blush, maroon, and white which made everything easier to mix and match especially accessories like hats and scarves. It was definitely cold so layers were my best friend!
Here is everything I packed to wear on the trip with me.
I had the absolutely best time in Chicago and would highly recommend planning a trip if you’ve never been!
Totally saving this as well as your other Chicago post for my work trip there this summer! The view from that rooftop looks AMAZING.
xoxo A
http://www.southernbelleintraining.com
Yes, I highly recommend checking out Cindy’s Rooftop! I can’t wait to hear about your trip!