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Cheap (& Free!) Winter/Rainy Day Date Ideas in Chicago

Being long-distance, Dalton and I usually try to make the most of the weekends that we visit each other. We are always on a limited schedule, so we're often packing a lot of activities into a very small window of time, and given the moody weather that Chicago likes to put on display between October and April, this can get tricky! 

Sometimes we have a hard time coming up with fun and new things that we can do when the weather doesn't always have you dying to linger outside. We also like to avoid breaking the bank, since we're already spending a good amount of money on flights here and there. 

Thankfully, Chicago has a pretty endless supply of fun (even in the winter or rain), so over time we've picked up a few pretty great date night ideas that work no matter what the weather is! Here are some of our favorites:


1. Whirlyball - I heard people talk about this off and on after I moved here, but it sounded like a made up place to me. Now that I've done my research, it's next on our list! They have bowling, laser tag, and a very unique game called Whirlyball that seems a little bit strange and equally awesome. We love being active and finding fun new experiences, so this is perfect on a day that we need to be stuck inside. 

2. Second City Comedy Shows - You've likely heard of this famous venue, considering a large amount of SNL comedians got their starts right here in Chicago. The shows are surprisingly super affordable (usually around $14 per ticket), and absolutely hysterical. If you've already been, you could also try the Laugh Factory, which I've heard great things about! We love to make dinner and have drinks at home before heading over. 

3. Ice Skating Downtown -  This one may seem a little bit obvious, but I think it's always fun (not just at Christmas). The views you get while you're surround by the Chicago skyline are unparalleled. If you aren't interested in skating in circles, you could also try the new Ice Skating Ribbon right next door! 

4. FTW  - This arcade bar with cocktails, lounge areas, and a mini golf course themed after Chicago landmarks got some seriously high praise from my roommate, and we can't wait to check it out. I love that it's a good spot to both hang out, and get a little bit competitive. Plus, if the arcade games get tired, you can walk right next door to Lucky Strike!

5. Lincoln Park Conservatory - If the terrible weather has you feeling in a particularly dreary mood, try heading over to explore the warm (and humid) pathways and flowers in the Lincoln Park Conservatory. It's open to the public, and it's a great way to walk off a huge dinner at the famous Pizza Oven & Grinder Co. which is a short walk away. 

Winter weather, torrential downpours, and 450 miles hasn't been able to cramp our date-night style, so don't let it put a downer on yours either! Have fun exploring!

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