Chicago Spring Date Ideas Manny and I love

March 31, 2023

Manny and I don’t get out now together as much as we would like BUT we did just get a new babysitter, so I am hoping we can do some spring dates soon! Here is a list of things we have all done that would be fun for a spring date!

Food & Drinks

Malt Row Crawl

For all the beer lovers out there (but a few like Koval and Forbidden Root have wine + cocktails!), create your own beer crawl! Malt Row in Ravenswood is home to a ton of craft breweries, an award-winning distillery, and a winery! We did this in the fall and want to go back again when the weather is nice. We did Dovetail, Begyle, Forbidden Root and Koval (which is dog and family-friendly + they have a brand new space) This area is super walkable and accessible from the Brown Line. You can end the day at Spacca Napoli, which has some of the best wood-fired pizza! There are also plenty of restaurants and shopping in the area. Check their official guide here!

Create your own Albany Park Food Tour

We did a food crawl date night for our wedding anniversary through Albany Park recently and went to so many great spots to enjoy food from all over the world! It was the perfect spring date night in Chicago! Here’s our round-up:

Subo Flipino Kitchen, Hot Dog Station, Cilantro Taco House – Mexican, Pisco Peruvian, Antepli Turkish Gourmet for desserts, Lindo Michocan – Mexican, Atitlan Restaurant – Guatemalan, Dulce De Leche Cafe  – open until 4pm, great for brunch and coffee!

I would also stop in at Bokeh for some cocktails and mocktails! They are amazing!


I love a patio lunch with a view @robertspizzaco in Streeterville. It’s on an inlet along the river! The pizza is really, really good and it’s nice to dine along the river if it’s nice out.

I love the a good brewery with a view like Metropolitan Brewery in Rockwell on the River in Avondale. You can sit inside or outside on their patio. Soul & Smoke just opened a new location there too so you can grab food and sit at the brewery. There’s always lots of families, groups of friends, dogs and nice to sit along the river! 


See a show

If you haven’t been to the iconic Music Box Theatre, it’s a Chicago landmark! They have Back to the Future and Forest Gump playing in April. When it’s a cold, rainy spring day, this would be fun! I’m also convinced it’s haunted…but that’s another story of when I toured it 🙂

This is actually on our bucket list, but we want to see Paper Machete at Green Mill! I love love the Green Mill and in my late 20’s would go ALLLL the time. It’s iconic. Right now, every Saturday at 3pm, Paper Machete has a FREE performance with music, comedy and more! I think this makes such a fun date or out friends. Honestly, I’d go alone too. Haha


Explore Pilsen

Pilsen is one of our favorite neighborhoods for the food and culture! When it’s a nice spring day, take a walk to see all the street murals, explore the National Museum of Mexican Art, and then have dinner at 5 Rabinitos or La Mejikana. There is a such good shopping too. The vintage shop on 18th is amazing. End the night at a nightcap at La Luna or Del Toro.  I have a whole itinerary that includes a day in Pilsen here if you want even more ideas!

Flower Shows at the Conservatories

Both conservatories have Spring Flower Shows right now. We love the Garfield Park Conservatory! We actually just went and you can see it here. It’s free (just make sure to make reservations online- weekend slots fill quickly!), so warm inside and tropical feeling. It’s a nice rainy, spring day date thing to do. My kids loved it too. Just make sure to book a few days in advance.

I hope some of these gave you some spring date ideas!If you need more spring ideas, here is my bucketlist. Let me know if you checked any out!


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