a weekend in chicago.

A Weekend in Chicago.

A few weeks ago I made my return to Chicago – it was my first time back since we moved and although it was a bit strange to be in town as a visitor, it was one of my favorite weekends ever. There’s just nothing better than Chicago in the summer! I’ve gotten a few questions about Chicago favorites and recommendations so I wanted to share a run down of how I spent a long weekend in the Windy City:

A Weekend in Chicago.

Where to StayAfter doing a little staycation at The Thompson right when the hotel opened I immediately knew I wanted to book a room for myself when planning this trip. From the decor to the staff and service, there’s no better hotel in Chicago than The Thompson. I ended up being upgraded to a suite and it was AMAZING – the downtown views, huge bathroom and ultra-comfortable king sized bed were a dream and I’m already looking forward to going back. The Thompson’s restaurant, Nico Osteria, is also incredible – we had a goodbye dinner there with a coworker right before we moved and it was one of the best meals of my life! I also recently discovered that The Thompson is not only pet friendly, but they have no size restrictions or additional pet fee. Callie may be coming with next time ;)

A Weekend in Chicago.

What to Eat: My friends were teasing me throughout the trip because whenever they’d ask what I wanted to do, I’d reply with a restaurant I wanted to go to. We spent a large portion of my way eating our way through my favorite restaurants and satisfying cravings I’ve had since moving out west. A few all-time favorite spots:

  • Gilt Bar (River North): I had my cab driver take me directly from ORD to Gilt Bar to meet up with my best friend for cocktails immediately after arriving back in Chicago. Gilt Bar is probably my favorite bar of all-time because of the dark and cozy atmosphere, cool decor and amazing cocktail menu. Their food is also great, don’t miss the garlic toast and mussels.
  • Chicago Q (Gold Coast): First off, I love the fact that Q is led by a female chef (girl power!) but most of all, I just love how damn good the BBQ is! We started with cocktails – the spicy margarita was SO good! – and then grabbed a bottle of rose to go with our entrees and gazillion sides. The BBQ chips and homemade pickles they bring as a starter are super addicting and I always get the pulled pork platter with coleslaw and their honey cornbread.
  • Big Star (Wicker Park): Fact: tacos just taste better when eaten al fresco. Big Star is cash only and can have a serious wait for a table (no reservations, unfortunately) but trust me, it’s worth it. Absolutely order a pitcher of margaritas, but beware – they’ll sneak up on you! I’ve tried all of their tacos and they are all the best tacos of my life and in my book, Big Star is one of the most quintessential Chicago summer spots in the entire city.
  • Little Goat Diner (West Loop): I caught up with Kit and Erin over brunch at Little Goat and basically wanted to eat everything on the menu (as usual). Start with an iced coffee and a warmed up cinnamon roll for the table to split – if you’re going savory, try the corned beef hash, and if you’re in the mood for sweet, try the blueberry pancakes.
  • Restaurant Beatrix (River North): River North was the last neighborhood I lived in and Beatrix has always been a favorite spot of mine – everything on their menu is fresh and it’s definitely a healthier option than many of Chicago’s hearty meat and potatoes spots. I’d recommend Beatrix for brunch or lunch; if there’s a wait and you don’t have a reservation, you can grab a seat at the coffee bar (and definitely get a coffee and a cookie while you’re hanging out there!)
  • Do-Rite Donuts (Streeterville): BEST DONUTS EVER. Period. Done. I can confidently make this statement because I have eaten every donut offering in Chicago but nothing is quite as good as Do-Rite. The Streeterville location is right by Northwestern and also sells fried chicken and breakfast sandwiches, which are also very tasty. Donut wise, go with the cinnamon crunch raised; it’s basically a cross between a donut, cinnamon roll and coffee cake and it is life changing.
  • Siena Tavern (River North): Siena Tavern is a perfect spot for happy hour or date night – the food is awesome and they have a great cocktail and wine list. Don’t miss their pizzas and be sure to save room for gelato after your meal.

A Weekend in Chicago.

What to Do: First of all, if you’ve never been to Chicago, please book a trip immediately and visit before the summer is over and I promise you, you will not regret it. A few things to do during your trip:

  • Flywheel Sports (River North & Old Town): It felt SO GOOD to be back with my Chicago #FlyFam! You’ve already heard me rave endlessly about Flywheel but there is no better way to get your butt kicked in only 45 minutes while having an absolute blast. Alicia, Candy and Michael are my all-time favorite instructors – if you have a chance to take a class with them be sure to ride bike 16 in my honor ;)
  • Fireworks on the Lakefront: After a few too many glasses of wine we wandered over to Oak Street beach and walked south around the bend and plopped down on the lakefront trail for the Navy Pier Fireworks show – the view was perfect and it was one of my very favorite moments of the trip.
  • Stand Up Paddleboarding (North Ave. Beach): I was looking to do a new activity while I was in town and convinced my best friend to go SUP on Lake Michigan one afternoon. The waters were a little choppy (I fell in, twice) but the views of the skyline were incredible and it was so much fun to be out on the water. Highly recommended!
  • Blowout from BloHaute (wherever!): By now you already know that getting a blowout is awesome but you know what really takes the cake? Getting a blowout without having to go to a salon. Convenience at its finest, my friends! I checked out BloHaute while I was in Chicago and it was a serious game changer – they send a stylist right to your apartment or hotel and make you look like a million bucks even if you’re still in your pajamas (like I may have been). My stylist April was the sweetest and even dealt with my overgrown bangs by braiding them back in a little french fishtail, which was the coolest thing ever.

It was SO good to be back and the trip went by way too quickly – I’m already dying to go back for another visit and honestly cannot recommend Chicago enough as a perfect place for a weekend trip. Let me know if you’re ever heading there, I’m always happy to share additional recommendations!