8 Unique Date Night Ideas in Chicago That Are Sure to Impress Your Date

Dates are the glue to any relationship. Maybe you and a prospective partner have just started dating and are using this time to get to know each other. Maybe you’ve been in a relationship for a year already. Maybe you’re newlyweds. Maybe you’ve been married for forty years. No matter what stage of a relationship you’re in, dates are that special time when you and your partner get to spend time with each other and only each other.

There’s nothing wrong with a classic dinner and movie date, but sometimes it doesn’t hurt to spice up your routine with something a little new. This weekend, test out one of these more niche date ideas and see what your date thinks of it. Who knows? Maybe that venu that’s new to you today will become a lifelong favorite haunt for you and your partner for years and years to come.

About GiftYa

Hate trying to decide who should pay for the date, or whether you should just split the check or each pay your own way? GiftYa understands that, and that’s why they’ve made it their mission to take the pain out of paying for dates with e-gift cards. Send one of their partners’ e-gift cards to your significant other for a special occasion so they can “pay” for your date the next time you decide to go to that place. Better yet, send one to your other favorite couple so neither one of them has to pay!

Petit Margeaux

Waldorf Astoria Chicago, 11 E Walton St, Chicago, IL 60611 | Gold Coast | facebook.com/petitmargeaux

A trip to Paris would be one expensive date...but why bother when you’ve got an authentic Parisian cafe right in Chicago?

A trip to Paris might be a little too much for a first date, but bring them to Petit Margeaux for just a taste of French Champagne. Image courtesy of Petit Margeaux Facebook.

Have you and your partner been saving up for a trip to Paris but haven’t quite reached your goal yet? No worries! Tucked away on the ground floor of Chicago’s Waldorf Astoria hotel is this Parisian-inspired gem.

A self-proclaimed French patisserie, this little cafe serves up anything from some of the most beloved coffee in Chicago, to sweet treats, to brunch! The cozy and chic interior will almost make you feel like you’re really in Paris.

Stop by for a taste of France served up with the Midwestern hospitality you know and love.

“Super cute little bakery and cafe. I had some delightful little pastries there and my girlfriend enjoyed a bit of cheesecake. Staff was friendly and helpful. We just had a lovely little afternoon there.” - Yelp Review


Wildberry Pancakes and Cafe

130 E Randolph St, Chicago, IL 60601 | The Loop | wildberrycafe.com

Breakfast dates are underrated. Swing by Wildberry for some of the best breakfast food in Chicago!

Say yes to pancakes for brunch with your date this week. Image courtesy of Wildberry Pancakes and Cafe Instagram.

Waking up early just to go out for breakfast probably isn’t high on your list of date ideas you absolutely have to try, but you might just want to make an exception for Wildberry Pancakes and Cafe.

Located in the heart of all of the hustle and bustle of Chicago, this breakfast joint is a favorite among many of the locals. During peak times, you can find yourself waiting for a seat for up to three hours!

Stop in to try the wildberry pancakes they’re most famous for, or maybe decide on something a little more savory like the barbacoa chilaquiles.

Pro tip: add your name to Yelp’s waiting list for a guaranteed spot if you aren’t as much of a morning person and hang out at a nearby coffee shop until they tell you your table’s ready.

“Amazing dining experience! The best service hands down.  The hostess was so friendly and accommodating, our waitress was friendly, fast and brought to-go cups for our unfinished lattes.” - Yelp Review


2683 N Halsted St, Chicago, IL 60614 | Neighborhood: Lincoln Park | aliveone.com

Live entertainment has never sounded more, well, alive than at this intimate Chicagoan dive bar.

Live entertainment is a sure-fire way to impress your date this weekend. Image courtesy of aliveOne Instagram.

Do both you and your date love live entertainment but not sure you want your first date to be at a concert where you can barely hear each other over the music? aliveOne is a great compromise. 

With live music shows from local musicians every week, karaoke nights where the two of you can make fools of yourselves in front of a crowd - and receive the same entertainment in turn - and regular comedy shows, there’s bound to be something here that you’ll both enjoy.

With a fairly intimate space, but a roomy back room fit for shows, you’ll still be able to chat while you enjoy the entertainment - as well as some tasty drinks!

Buy a GiftYa to aliveOne >

“There is something going on every night of the week in the back room from comedy to trivia to karaoke and live bands and the only thing that beats their happy hour special is the staff.” - Yelp Review

Cold Storage

1000 W Fulton Market, Chicago, IL 60607 | Fulton Market, West Loop | coldstoragechicago.com

Nothing fishy about this date (except the menu)!

If your date is a seafood fan, you definitely won’t want to miss out on the opportunity to take them to Cold Storage! Image courtesy of Cold Storage Instagram.

The last thing you want when you take someone on a date is for them to think you’re a suspicious character. While this seafood restaurant is packed with a fishy menu, nothing about bringing a date here is fishy.

Fine dining seafood has never been quite so, well, fine. You’ll have to try their oysters, which people tout as some of the best in the entire city! We hear the lobster bisque is pretty amazing, too.

Buy a GiftYa to Cold Storage >

“The oysters aren't your regular dollar oysters. They are big, thick, and juicy!! And I'm not exaggerating, some of them were OVERFLOWING out of the shell. SO good.” - Yelp Review

The Owl Chicago

2521 N Milwaukee | Chicago, IL 60647 | owlbarchicago.com

For a late-night date, this one will be a hoot!

You might think a casual date for drinks is mundane, but as soon as you join the crowd of party people at The Owl, you’ll realize it’s anything but there. Image courtesy of The Owl Instagram.

Are you and your date social butterflies? Do you like to stay up late? The Owl is one of Chicago’s best late-night party spots.

Open until 4am every day, you can stop by whenever it suits you and get to know other couples like you while you flit around the room. Be sure to try one of their signature drinks for the best experience!

“We love everything about this place. The atmosphere, the bartender, the happy hour specials are especially great, good jukes.” - Yelp Review

Duck Duck Goat

857 W Fulton Market, Chicago, IL 60607 | Fulton Market, West Loop | duckduckgoatchicago.com

Chinese take-out is always a great idea, but you probably won’t want to miss out on the chance to dine in at this Chinese restaurant with a twist!

Recipes for dim sum put together by a celebrity chef? Your date is sure to be impressed! .Image courtesy of Duck Duck Goat Instagram.

Has your partner always wanted to try some food made by one of those celebrity chefs you always see on TV? Stephanie Izard, who made her name by winning Top Chef several years ago, is the owner of this Chinese restaurant in Fulton Market.

While you probably won’t find her cooking up your meals herself, she did create all of the recipes you’ll see on the menu, which combine classic Chinese cuisine with bold flavors you might not expect.

Split some dim sum and make a note of everything you can taste in your meal. Next weekend, you can try to recreate it just for yourselves at home!

Buy a GiftYa to Duck Duck Goat >

“To be honest... we had a hard time picking a favorite. Everything is just so incredibly flavorful and the more dishes that come out, the more your jaw drops.” - Yelp Review

Estelle’s cafe & lounge

2013 W North Ave | Chicago, IL 60647 | estelleschicago.com

Amazing food and a large selection of beers? If your date isn’t already in love with you, they may be soon!

If you’re looking for good food to pair with some first date conversation, the atmosphere at Estelle’s will provide the perfect backdrop to your date. Image courtesy of Estelle’s Instagram.

First dates can be exciting, but they can also be a little awkward at the very beginning. A dive bar might be the perfect place for you and your date to break the ice and really start to get to know each other. 

Share some burgers, which regulars have deemed some of the best in the entire city, and peruse their extensive beer list until you each find something you like. It’s hard to feel awkward around anyone when you’re sharing food and drinks and laughs.

“The service was refreshing, nice attentive service with a friendly bartender.  The food options are typical of dive bars, but are top notch.” - Yelp Review

Broken English Taco Pub

2576 N Lincoln Ave, Chicago, IL 60614 | Lincoln Park | tacopub.com

Every date should feel like a fiesta...and this taco pub serving street-style tacos will give you just that!

Tacos are an absolute must for any couple looking to go out on the town for a bit. Image courtesy of Broken English Taco Pub Instagram.

Everybody likes tacos, and we’re betting you and your partner will love these authentic street-style Mexican tacos. Soft, freshly made tortillas packed with the fillings of your choice? Yum!

Whether you prefer all veggies or something with some meat, they’ve got something for everyone - and the drinks aren’t bad either. Stop by for a fun time filled with beautiful artwork, funky music, and the best tacos in Chicago.

Buy a GiftYa to Broken English Taco Pub >

“Just a chill, affordable taco pub with good food and $5 margaritas on Thursdays. I came here on a Thursday night with some friends. We all had a few margaritas and they were stroooong!” - Yelp Review

Your date is bound to be impressed by any one of these places. Good times and an amazing variety of food and drinks await you in Chicago. Go and see what they’ve got to offer!

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Trae Bodge

Trae Bodge is the shopping expert here at GiftYa. Trae helps people find the best deals and ideas on popular new items to purchase.

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