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Samantha Maloney

Valentine's Date Ideas Chicago

Valentine's Day is just under a month away so here are some fun Valentine's Date night ideas in Chicago. If you're being frugal, just pick 1 of 2 from the list and plan a date on a budget. It doesn't have to be extravagant, it's about just being together. Remember to make your reservations soon so you don't miss out as some of these places will most likely book up for Valentine's Day!


Cooking class

I’ve always said I don’t like cooking I prefer eating BUT I do love a cook cooking class. I’ve done a couple in my 30 years and it's always a blast. I’ve done group classes at places like the Chopping Block and just last year my now husband, Conor,  and I did a private class with a smaller group that was also really fun. We made all kinds of new things like ceviche! Since the group was much smaller it was definitely more intimate. If cooking classes aren't your thing you could always go with a mixology class, wine tasting, or even a wine-making class at somewhere like Wild Blossom Meadery. In addition to cooking and winemaking, there are so many other craft class options all around Chicago. You could do paint and sip, leather making, Rug making, stained glass, candle making, I could go on! 




Drinks on a rooftop

Why not kick off the night with some pre-dinner cocktails with a view?! Chicago has the best skyline and some of the best rooftop bars (not biased…or maybe I am) Cindy's rooftop is across from Millennium Park with gorgeous views of the lake. Offshore is located in Navy Pier, doesn’t get more Chicago than that! London house is always a favorite with stunning views of the river. 



View from Cindy's rooftop Chicago


Romantic dinner

You can't go wrong with a romantic dinner. Quiet chatter by candlelight is sure to set the mood. Having been together for almost 10 years, Conor and I have been a numerous dates so these are just SOME of the date night restaurants we love 


City cruises - Use promo code VDAY20 for 20% off Valentine's day cruises!

Carnival - All-you-can-eat brunch buffet $55 for adults on February 11th!


These are a little more on the expensive side BUT restaurant week in Chicago just started and while it won't continue until Valentine's Day, this is a good way to check out some restaurants you’ve been wanting to try and have an early Valentine's date. Or even come back for a V-Day dinner if it's in the budget! I listed all my restaurant week faves over on my IG (@windycity_sam) so be sure to follow me 🙂



Couple outside Carnivale Chicago


Staycation 

Nothing wrong with staying in on Valentine's Day…in a luxurious hotel that is! Order some room service while you relax and take in an amazing view. Chicago has tons of beautiful hotels to stay in and you can usually find a good deal if you look around. I’ve always used Expedia to track hotel dates and prices and I love it. They show you all the prices in an area plus you earn points on every purchase with OneKey (not sponsored I just love Expedia!) 


Do some sightseeing

Remember the bean is under construction! So unfortunately you won’t be able to see the bean BUT there are a few other sightseeing options: Ride the Centennial Wheel at Navy Pier,

Skydeck Chicago, located in the Sears Tower (I’ll never call it Willis…you can’t make me!) gives you a beautiful 360 view of the city OR you can try TILT, an observation deck that tilts out over the skyline in the John Hancock center. They have a bar on the 94th floor as well, the Cloud Bar. 


See a show

Theater Week in Chicago is Feb 8th - 18th, the PERFECT time to get a deal on theater tickets! You can get tickets starting at $15 so definitely affordable and there's a ton of shows and theaters participating this year. I saw a few shows with tickets starting at just $5! Here are some of our favorites:


Teatro Zinzanni

Drunk Shakespeare

Blue Man Group

In The Heights

Zanies


Just to name a few! The full of shows and where to buy tickets can be found at ChicagoTheatreWeek.com



 couple outside nederlander theater hamilton


Go casual with drinks and games

The more casual you go, the easier it can be to be frugal. If you want to just have drinks and apps we love Punch Bowl Social in Fulton Market. They also have games and darts so this can be done fairly inexpensively. You could also go somewhere like Flight Club Chicago for darts and drinks as well. Another option would be Beercards where you can grab drinks and play old-school arcade and pinball machines. It’s a great way to channel your inner child and have a few laughs!


I hope this list helps you come up with a few fun Valentine's Day date ideas in Chicago! There are so many fun things to do around Chicago, even during the cold weather. Have a great Valentine's Day! ❤️


Until Next time!

xoxo Sam


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