Better than Fireworks: A Chicago Staycation

I’ve written before about how much I love Chicago; and this weekend, I decided to REALLY love Chicago.

Rather than getting a group of friends to go away for the weekend, my friend Benjamin and I planned a “staycation” for Fourth of July Weekend. And what a weekend it was.

Benjamin and I worked Wednesday night to come up with a fun-filled schedule for what we called “Better than Fireworks: A Chicago Staycation.” (Each year, I find Fourth of July fireworks to be pretty mediocre, and I’m always wishing I had other, non-firework plans.) We publicized it to some friends, asking them to RSVP for whichever events fit their interest and their calendars. Throughout the weekend, we had 37 people participate. We took buses, cabs, L trains; we walked, ate, lounged, learned, and laughed. I think I gained six new Facebook friends.

Here’s the schedule:


7 p.m. Services with YAD (Young Adult Division) at Anshe Emet

  • We began the weekend by attending lively services with dozens of young adults from around Chicago.

10 p.m. Board games

  • People gathered at my apartment for a night full of Connect Four, Bananagrams, and other fun games until the wee hours of the morning.


10 a.m. Shabbat and Kiddush at Anshe Sholom

  • Those who wanted a Shabbat prayer experience gathered at Anshe Sholom. I arrived for the “11 o’clock minyan.” We then had a nice kiddush at the synagogue.

1 p.m. Picnic at Belmont Harbor

  • We grabbed some bread, chips, dips, and fruit and headed to a shady area by the beautiful Belmont Harbor. (Though bug spray would have been a welcome addition!)

4:30 p.m. Nap time at your own apartment

  • We needed it.

8:45 p.m. Dinner at Ed Debevic’s

Dinner at Ed Debevic's
  • A trip to Chicago is not complete until you get yelled at by your waiter. We had a great time wearing the standard headgear at this classic ’50s diner.

11 p.m. Karaoke at Sakura in Chinatown (if you’re going to click on that link, turn off your sound first)

Karaoke at Sakura
  • Apparently for $30, you can get a private room for eight people for an hour of singing. We had a great time showing off our voices to our favorite tunes (including “Man, I Feel Like a Woman” and “Wonderwall”). After our private room time ended, we joined the rest of the crowd to listen to other people make fools of themselves. I’m proud to admit that over the course of the night, the girls belted out the Spice Girls’ “Wannabe” two separate times.


2 p.m. Beach time at Montrose Beach

  • The sun was out, the E. coli levels were reasonable, and someone brought watermelon. Sounds like the perfect beach day. (Though I’m still tasting sand.)

4:30 p.m. Shower time

  • What kind of a schedule would this be if we didn’t allow for cleanliness?

6:30 p.m. Dinner at Pick-Me-Up Cafe in Wrigleyville

  • We crowded 14 people into the kitschy restaurant’s biggest table and had a great time with this vegetarian- and vegan-friendly restaurant. I’d say this is the best grilled cheese I’ve ever eaten – get it with pesto mayo – but the pasta salad left something to be desired.

8 p.m. Improv Olympic

  • Arriving slightly late from our delicious dinner, Staycationers spread themselves around the iO Theatre for a night of long-form improv, part of which apparently turned into a 20-minute spoof of Three’s Company.

10:30 p.m. Bowling at Southport Lanes

  • This is not your typical bowling alley. At Southport Lanes, there’s a little man (I only assume he’s little…he’s probably normal-sized) working behind the lanes, setting and re-setting the pins after each turn. And – no joke – if he liked you (or if you were a pretty girl), he’d knock down those last few pins for you; and if he didn’t, he’d lift up a pin and put it back right after your turn ended. It was like human bumper bowling. When you factor in the Groupon Now deal we got, the whole thing only cost each of us $2. Not bad for an event that might have been one of the top highlights of the weekend.
Bowling at Southport Lanes


2:30 p.m. Chicago History Museum

  • Clearly, I love Chicago; and this museum is no exception. This was my third time at the museum, but each time I go, I love learning new things about my favorite city. (I’ll buy an ice cream for the first person who correctly comments on this post with what the four stars on the Chicago flag represent…no Googling!) The museum was free for the Fourth of July and was a great way to celebrate staycation location.

4:30 p.m. Snacks at the Fudge Pot / Explore Old Town neighborhood

  • It’s hard to pass up this fudge shop in Old Town. We got some delicious fudge, chocolate-covered bananas, and other treats, and enjoyed the fun Old Town shops and parks.

6 p.m. Dinner at Edwardo’s Pizzeria

  • Best pizza in Chicago. I’m talking to you, Giordano’s, Uno’s, and Lou Malnati’s. Best pizza in Chicago.

8 p.m. Second City – “Fair and Unbalanced”

  • This comic relief – a mixture of sketch comedy and improv – was a great way to end our fantastic Fourth of July weekend.

And now, we’re all exhausted. But we had a great time exploring our city, meeting new people, and trying lots of new places. And finally, after 24 years, I figured out a way to get out of fireworks!

Who’s ready for the next adventure?


7 thoughts on “Better than Fireworks: A Chicago Staycation

  1. I’m so impressed with the time, energy and passion you put into this! Congratulations on a successful weekend!

  2. Fort Dearborn, Chicago Fire, Columbian Exposition, Century of Progress Expo.

    Because I think Google would argue that their name is a non-Generic trademark, and even though on a normal day I wouldn’t agree, I have successfully acquired that information without “Googling.”

    Went straight to the source. Wikipedia.

    You owe me an ice cream.

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