Fall Double Date Ideas in Chicago

Fall Double Date Ideas in Chicago

Ahhhhh fall, the season of pumpkin-spiced everything, apple picking, football and cuffing. Fall is pretty much your last first impression before winter. Whether you’re trying to connect with a new Bumble match or keeping the summer romance alive into fall, I’ve rounded up some sweet fall spots to have a little fun fall double date night in Chicago with your boo. Honestly, I love date nights but appreciate double dates. I went on most of these as fall doubles dates in Chicago and had some memorable nights.

Double Date Game Night at Whirlyball:

One of my most recent double date nights in Chicago was on the west side. Just off the main streets in Bucktown, past Map Room and some west side staples, is an iconic staple to Chicago – Whirlyball. Step inside for a night of fun for a group date or double date.

Fall double date ideas in Chicago - Fire pit at Whirlyball in Bucktown.

Dinner is always nice. I do love a few rounds of cocktails and connections, but having an activity to break the ice and add in some competition is a recipe for a fun fall night. Whirlyball is more than it’s namesake (though I would definitely check it out). They have bowling lanes and amazing servers that bring hot wings, pizza and cocktails to you. So, you only have to focus on turning your gutter ball into a split.

Fall double date ideas in Chicago - bowling at Whirlyball in Bucktown.
Bowling at Whirlyball

Whirlyball is basically a palace of fun. Around the corner from bowling, they have bumper cars. And this fall, you can enjoy your nightcap by the fire pit.

I did a double date night with my best friend and we ate wings and played two rounds of bowling. I met her boyfriend, who I’m pretty sure only knew how to get strikes. They always broke 100 but I was happy with 70ish.

Coffee Cocktails and a Sunset Stroll by Lake Michigan:

It wouldn’t be a fall date without pumpkin spice lattes and Rewired has specialty ones like the Pumpkin Jack Lattes, which you can enjoy by the fire on the patio.

We started our evening on the beach taking a nice stroll after work and then headed to Rewired, which was only a few blocks away. Pro tip: if you’re going during a Saturday afternoon, you can grab coffee cocktails to go and sip them on the beach.

Fall double date ideas in Chicago - coffee cocktails at Rewired in Edgewater.

They added a fall forward cocktails to the menu including the Pumpkin Spiced Mule. The Peaches and Dreams cocktail has a velvety texture and a crushed graham cracker rim with a whiskey base, orange butters and brown sugar.

Rewired is a cute bar and pizza place, but actually looks like a coffee shop when you pass by. People will study or read – they have bookshelves filled with books and games.

When I tasted the food, I thought, finally, intellectuals get to eat good, gourmet food. Usually coffee shops in Chicago don’t have a lot of food options, but Rewired has pizzas and gourmet apps.

Fall double date idea in Chicago  - gourmet appetizers like buffalo cauliflower bites at Rewired.

Some of my faves were the apple walnut vinaigrette salad with watermelon radish, the beer battered buffalo cauliflower with house made ranch, and the beer battered fried pickles with chipolte mayo.

But save room for pizza. They make specialty pizzas including fried chicken pizza (with chicken, bell peppers, cheddar and ranch), an al pastor pizza (pork, pineapple, pickled onions and green salsa) and onion soup pizza (caramelized onions, white sauce and parmesan).

Honestly, restaurants should start serving more white sauces pizzas. They are so good!

A few rounds of pumpkin spiced drinks, and slices of pizza and a game or two, and it makes for a lovely evening.

Rewired also has trivia nights on Monday’s if you’re in the Edgewater neighborhood.

Double Date Trivia Night at The Rambler:

The Rambler Kitchen & Tap has a Name That Tune Trivia every Tuesday at 7 p.m. And it’s popping. The bar is right in North Centre and Has a cute patio and beer garden. They also have football watch parties. P.S. it’s an Iowa bar.

I didn’t think I would be that good at trivia – and I’m not. But that’s why I brought smart friends with me and it turns out my boyfriend is a genius when it comes to obscure music trivia. We all enjoyed dinner including the French dip and pork tenderloin sandwiches and Buffalo chicken wraps. And then had a few rounds of beer.

Trying out the giant pork tenderloin sandwich. It’s giant!

The last question of the night was: Name the two hip hop artists who each released an album during the 2010s (2010-2019) that went to #1 on the Billboard 200 chart. The following clues a) each has a two word alliterative stage name and b) if you took the second word of the stage name of one, and added two letters, you would get the second word of the stage name from the other.

My friends, Sohaib and Megan joined my boyfriend and I for trivia night.

Let me know if you get this. My boyfriend guessed right and won our team second place.

Fall double date ideas in Chicago - The Rambler Kitchen and Tap for Tuesday Trivia nights.
My boyfriend and I in the beer garden.

We all got tequila shots to celebrate. Honestly, game night is so much fun and I forgot how great it is to go out during a week night to break up the week.

Fall Double Date Ideas in Chicago:

So there you have it. Three fall double date ideas in Chicago. It’s nice to get out and play some games and enjoy the fall weather before it gets too cold. If you’re looking for more date activities- here’s how I planned a weekend road trip from Chicago. Happy date night!

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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