Chicago Sister Weekend

The Keegan sistas take on Chi-town!! & it was the best, most wonderful, absolutely freezing weekend EVER; filled with deep dish pizza, irish pubs, art museums &.. we somehow even mustered the energy for a soul cycle class. Go us!

So where to begin? We did so much in 72 hours, more than any of us expected! To keep it simple, I’ve rounded up our Bucket List with our favorite spots during the trip.

One major highlight of the weekend was the location of our hotel. We stayed at the Dana Hotel & Spa, which was perfect for our short getaway, located only 3 blocks from the Magnificent Mile, and close to lots of shopping and restaurants. We were able to walk to many places which was a huge plus.

Since it was chilly on Saturday, we opted for the Art Institute of Chicago after brunch at The Hampton Social. We spent almost three hours at the museum, and it still wasn’t enough time. Afterwards, we headed to Giordano’s, to get the BEST deep dish pizza. Yum! Then we rested, drank some Trader Joe’s wine in our hotel & walked over to The Flamingo Rum Club, a Cuban-inspired cabaret, which had the best music and drinks!


  • Museums: Art Institute of Chicago, Museum of Contemporary Art, Museum of Science & Industry, Chicago History Museum, The Field Museum
  • Coffee/Cafes: Goddess & The Baker, The Wormhole Coffee, Sawada Coffee
  • Cocktails: Cindy’s Rooftop Bar, Flamingo Rum Club, Restoration Hardware, Drumbar, The J. Parker
  • Brunch: The Hampton Social, Wildberry Pancakes & Cafe, Trench
  • Brewskis: Howl at the Moon, The Galway Arms, O’Callaghan’s
  • Touristy Things: Chicago City Boat Tour, The Bean, Millennium Park, Skydeck Chicago, Navy Pier, Wrigley Field
  • Best Deep Dish: Lou Malnati’s, Giordano’s
  • Our Hotel: *Dana Hotel & Spa

It’s been so nice to have my sisters as friends as we’ve gotten older. At one point, we were all separated and it was really tough. I was studying in Spain, Katie was living in Milwaukee, Anna was in New York, and Liv was getting ready to leave for college.. it was hard being so far from each other.  I feel so lucky to have these three in my life. (Oh god, this is getting super cheesy.) But seriously, what would I do without them!?

If you’ve read my blog, then you know I’m a huge fan of living in St. Pete, but one of the best parts of being in St. Pete is that they’re here too. Liv in one more month! 

Friends always ask how the heck we all get along so well. Truthfully, I don’t think we’ve really stayed mad at each other for more than a few hours. I guess you can look at it this way, because we’re an even number of four.. odds are someone is on your side. (You just really want to make sure that someone is Anna.)

Shop Our Outfits!

Thanks to my sisters for letting me share the tiniest bit of our trip. You’re my real life girl gang & complete my #squadgoals. I love you little bitches.

photos by Julie Kennedy  / *thank you to Dana Hotel & Spa for sponsoring this post

Join the discussion 9 Comments

  • You all are adorable! Love Chicago.

  • Sharon says:

    Sometime when I need a miracle, I see my daughters – and realized I’ve created four❤

    Proud mama

  • Joan says:

    Everything about this is perfect 💋 (Especially that shirt and that braid!)

  • Mikey says:

    Lol ALWAYS want Anna boo on your side. Glad you girls had fun!

  • aunt aim says:

    Love you all to pieces ❤
    aunt aim

  • Anna Keegan says:

    Best sister trip! You captured all the fun moments. I’m so glad we have these to cherish. Love you!

  • Victoria says:

    You all look lovely! Chicago is one of my favorite cities, so pretty and so many things to do. With this post you just made me miss my sister, thanks God Im going to visit her soon 🙂
    Thanks for sharing this, Victoria

  • Sharon says:

    Whenever I’m feeling a little down, this post puts it all in perspective❤️ Love my babies

  • Alison Free says:

    Wow.. it’s like a professional photographer, hair stylist, designer, makeup artist and concierge was following them around! Now that’s some unique beauty and talent!

    From someone who know the strength, love and spirit of 4 sisters…

    A proud mom of 4 amazing girls❣️

    How lucky are we?! Just wait til they start having babies.. it will blow your mind!

    Thanks for sharing!!!

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