How to spend a weekend in Chicago

How to Spend a Weekend in Chicago

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This is a sponsored blog post, but my love for Chicago is all my own!

I live about five hours from Chicago, so it’s my go-to big city if we want to get away for a weekend. There is so much to do and so many good eats there. I’ve compiled a sample itinerary for you based on our most recent trip!

How to spend a weekend in Chicago

Day 1:

  • Check into your hotel. I really enjoyed taking photos last year inside Hilton Chicago, so we decided to stay here for a weekend!

    How to spend a weekend in Chicago: Hilton Chicago
    Hilton Chicago
  • See Southern Gothic at the Windy City Playhouse. This is a show unlike anything I’ve ever been to – the set is an actual house and you get to play a “fly on the wall.” The set itself was incredible – I had to chuckle – lots of the set was built even better than my house! When you first get to the playhouse, you can order drinks from the bar and mingle with the other attendees.
    Bartender making drinks at Southern Gothic
    Bartender making a Shirley Temple for my daughter
    Invitation to cocktail party - Southern Gothic
    Invitation to the party!
    Southern Gothic at the Windy City Playhouse in Chicago
    Welcome to the cocktail party!

    The scene is set at a cocktail party, where we get to witness lots of scandal and drama play out. They serve cocktails, and you can eat the food on the set.

    Cocktail drink at Southern Gothic
    I think this drink was called “Sparkles is Dead” which had gin, peach liqueur, lemon, basil, and a splash of rosé. I think I had four different drinks during the play.
    Snacks at the cocktail party - Southern Gothic
    Snacks at the cocktail party – my daughter thought that the graham crackers with frosting was amazing! There are also seats all along the edge of the set for you to sit.

    I took my 12 year old and she said it was the best play she’d ever been to, and I have to agree! I loved the voyeuristic production – you really felt like you were so much more involved because you got to eavesdrop everywhere! Be sure to stick around the front lobby area to get pictures with the cast!

    With some of the cast from Southern Gothic
    With some of the cast from Southern Gothic

    Southern Gothic at the Windy City Playhouse
    What kind of scandal do you suppose is going on?

Day 2:

  • Visit the Lincoln Park Zoo – it’s free to get in! They have all kinds of animals, such as polar bears, penguins, monkeys, and more. Not only that, but they have a carousel that the kids loved. Tickets for the carousel were $3 each.
  • See Blue Man Group at the Briar Street Theatre. Despite my associating them with a Vegas production, this is actually a super family-friendly show. In fact, most of the audience were families! I later learned that this production actually began in NYC over 25 years ago!

Some things to know: there is parking directly next to the venue for $15. Bring cash – it is worth parking here to save the trouble of finding parking elsewhere. Should you forget cash, there is a CVS around the corner with an ATM machine. There is also a bar with drinks and snacks inside the venue. When buying your tickets, if you pick seats up front, there is a chance you can get wet. They provide ponchos!

Blue Man Group mixes art, music, comedy and state-of-the-art technology, encouraging everyone to reconnect with their inner (and outer) child and see the world through a new perspective. Blue Man GroupWatching the actors was a lot like watching the Three Stooges, only much cooler. There were so many colors and they involved the audience! Who knows, you might just get picked to go on stage! Blue Man Group

My favorite part about the entire show was when they brought out these enormous lighted balloons. Imagine a lighted beach ball the size of a large shed…and multiple that by like 10. Check it out for yourself:

Blue Man Group in Chicago
Blue Man Group National Tour
Credit photo: ©Paul Kolnik
nyc 212-362-7778

Be sure to wait around in the lobby after the show – you can get your picture taken with the actors!

Blue Man Group Chicago
Get your picture taken after the show!


Recommendations for some good eats:

  • Hot”G”Dog, because having a Chicago dog in Chicago is essential
  • Lem’s BBQ House, where they’ve been smoking rib tips in Chicago for over six decades
  • Au Cheval, for Chicago’s most sought-after burger (expect to wait hours to get your hands on it, otherwise if you’re short on time, hit up Small Cheval in Wicker Park!)

Other notable attractions if you have time:

  • Visit “the bean” Cloud Gate – it is a 10-ton elliptical sculpture forged of a seamless series of highly polished stainless steel plates, which reflect Chicago’s famous skyline and the clouds above
  • Visit the Skydeck at Willis Tower if you dare, where you can step outside the tallest building in the Western Hemisphere. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck


I hope you like these suggestions! Let me know in the comments below what you think!


1 thought on “How to Spend a Weekend in Chicago”

  1. Pingback: 100 + Epic Bucket List Adventures - Idyllic Pursuit

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