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6 Fun Date Spots in Downtown Chicago

Downtown Chicago has so many great places to eat, it can be really hard to choose where to go sometimes! I Especially if you’re setting up a date and want to make sure you have both the vibe and food down: something casual, or a little more upscale? Just coffee, or dinner? Below are 6 of my favorite date spots in downtown Chicago that I’ve visited within the last year.


Casual Coffee Date: Sawada Coffee

Sawada Coffee is located in the same space as Green Street Smoked Meats, which automatically gives it an energetic yet casual vibe. The coffee drinks are just as beautiful and impressive as you’d expect from master latte art champion Hiroshi Sawada, with the Military Latte being picture-famous throughout Chicago. (There is also a matching donut available to nibble on!) This is a fun place for a date because if you’re nervous about things to talk about, you can always start with how pretty the drinks are, take part in a little people watching, or if you really need to loosen up a little, they also offer coffee drinks with alcohol!

Casual Lunch Date: Labriola Ristorante & Cafe

I visited Labriola Ristorante & Cafe during the warmer months when there was seating available outside, which I recommend if weather allows. They serve Neopolitan style pizzas, pasta, and also have a nice cocktail menu to select from. (If you’re really feeling romantic you can always share the spaghetti and meatballs a la Lady and the Tramp!) My arugula, mushroom and prosciutto pizza was delicious, and it’s perfect for sharing on a date. Stan’s donuts is also located next door, giving a fun option for dessert afterwards.

Dinner and Drinks Date: Baptiste & Bottle

Baptiste & Bottle is a “bourbon and provisions” bar located in the gorgeous Conrad Hotel in downtown Chicago. Actually everything is beautiful here, right down to the vintage glassware and plating of each dish. My favorite dishes were the Roasted Pekin Duck (persimmon, celery root, and gooseberry) and Day Boat Scallops (brown butter, sunchoke, pear). They also have an amazing drink list (I recommend trying the Huntsman: Glenfiddich and apricot), and if you are a bourbon/whiskey drinker, this is definitely the place for you! They have a great selection to choose from including Japanese whisky (I love Yamazaki!) and tasting flights.

Sushi Date #1: Roka Akor

I had to include two places for sushi because sushi is one of my favorite meals, and there are two spots I love equally downtown. Although Roka Akor is not unique to Chicago, it remains one of my favorite places to eat. It’s perfect for a sushi date: the atmosphere is pretty, the service impeccable and the dishes are super fresh and delicious. The Butterfish Tataki melts in your mouth and I don’t think you could go wrong with any of the sushi selections. The Lychee Bellini is a go to for me, and if you don’t feel like drinking something strong, there is also a selection of “mocktails” to choose from.

Sushi Date #2: Jellyfish

My second favorite spot for a sushi date is Jellyfish, which is located in the Gold Coast Area. It’s a smaller spot than Roka with a beautiful bar and lighting. Besides delicious sushi, the menu also offers other Pan-Asian fare (such as wagyu on a sizzling stone or shishito peppers with bonito flakes) and cocktails. I love elderflower so they also have one of my favorite drinks in Chicago, the Corsage: Cava Brut, Pur Likor elderflower, orange blossom water, Lavender bitters.

Casual Brunch Date: Hutch American Cafe

Hutch has two locations, with the Cafe located in River North. It is open for brunch every day with a happy hour from Monday-Friday. This is a cute little spot for “day after” brunch! The food is great with options for sweet (waffles and ice cream) to savory (chicken and biscuits). The Totchos (breakfast tater tots) are perfect for sharing. There’s also a selection of brunch classic drinks including a fun selection of mimosas, Bloody Marys, and boozy coffee drinks.

Roka Akor - Chicago
Hutch American Cafe

About the Author

Hello, I'm Melissa and I love to eat! I also like to make my tablemates wait while I take way too many pictures of my food before eating. :)