Chicago date ideas for when you messed up

Digging yourself out of the doghouse

So, your partner has you sleeping on the couch? Sounds like you messed up bad. Maybe you forgot your wedding anniversary or you had to work late on your partner’s birthday. Whatever your excuse, it doesn’t matter. The only thing that will help now is saying you’re sorry and going out of your way to make it better. It’s time to act fast, though. Don’t just stand there: Apologize to your sweetheart with an unforgettable date night in Chicago.

Chi-town can certainly put on the charm when it needs to, so allow it to mend your relationship problems and help you earn a place back in your honey’s arms.

Sunrise:
You can do no wrong with a strong cup of coffee, especially when you’ve dragged your love out of bed at the crack of dawn. Make the first stop on your redemption date be at the Robust Coffee Lounge, where you’ll order two honey nut lattes to go.

By this point, you’ve probably done enough rambling, so sit back and let nature do the talking. Set up shop down at Promontory Point to watch the sun rise over Lake Michigan. With dramatic views of the skyscrapers in the distance, this scenic overlook in Burnham Park will set the stage for a magical day in the city.

Breakfast:
To avoid entering hangry territory, make reservations for a table a Cindy’s. Perched on top of The Chicago Athletic Association Hotel, Cindy’s has an open-air terrace that will earn you major points. The rooftop scene serves up eggs benedict, buttermilk pancakes, and, oh, did we mention the sick views of Lake Michigan and Millennium Park? Order some sunrise potions, like the Full Bloom or Roman Holiday, for a well-deserved boozy brunch.

Mid-day adventures:
Now, the next part of your day really depends on you getting a good read on your partner. Anyone can get on board with a beautiful sunrise and brunch with a view, but believe it or not, not everyone’s down for messy deep-dish pizza and a trip up the Willis Tower.

Try something out of the ordinary like an architecture boat tour. Before you turn your nose up at the idea, consider a few things. First, it’s not every day that you can cruise on the Chicago River. Second, in addition to the architecture, you’ll get to see some pretty sweet views of the cityscape—hint, hint, romantic setting. Third, you’ll get props for thinking outside of the box when it comes to planning your date.

Viewfinder Tip: If you wind up at 5 Rabbit Cerveceria, sample the Chirimoya IPA and the 5 Lizard.

Afterward, take the edge off with a brewery hop. Getting a taste for the city’s brew scene is arguably one of the most fun date ideas in Chicago. It’s easy to hail a Lyft ride to get the adventure started, but the hard part will be choosing which breweries to hit up first. Begyle Brewing Company in North Center has board games and Skee-Ball to induce some friendly competition, while 5 Rabbit Cerveceria in Bedford Park reveals the first Latin-American inspired brewery in the states. Add Half Acre, Revolution, and Goose Island in the mix, and you’ll be feeling hoppy in no time.

Meanwhile, if your lover is still fuming, rent two bicycles to help burn off some steam. The Lakefront Trail is pretty much as picturesque as you can get, while the scenic North Branch Trail will lead you to the Chicago Botanic Garden. Hopefully after a few hours of cruising the cityscape, your partner will be ready to look you in the eyes again.

Dinner:
For dinner, step it up a notch with reservations at Geja’s Café. An intimate fondue restaurant decked out with candles and guitar players, it’s the perfect place to round out a romantic date in Chicago. Start off with a cheese flight, move onto the beef and lobster dinner, and then order the flaming chocolate desert fondue for the finale.

Evening:
It’s practically an unspoken rule that says if you can get your partner to laugh, they’re not allowed to be upset with you anymore, right? If you’re willing to give it a whirl, get a little help from one of the local comedy clubs. After all, this city is a beacon for rising comedians, so you’re bound to find a hilarious show, whether you get tickets to a class-act at The Second City or catch some improv at The Revival.

Overnight:
If you’re staying overnight, there are plenty of romantic Chicago hotels that are proud to be the cherry on top of your day. Consider a room with a view at the Waldorf Astoria Chicago, where you can soak up the Lake Michigan vistas from the privacy of your own balcony. Alternatively, when you stay at the Wyndham Grand Chicago Riverfront, you can both indulge with an in-room massage. Wherever you stay, you’ll find yourself pressed to top this date in the future.

What are your Chicago date night ideas?

Header image via Flickr/Phil

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Chloe Mulliner

As a staff writer for Expedia, Chloe Mulliner is dedicated to providing top travel tips for your jaunts around the world. She believes there are adventures to be had on every inch of the globe from surf spots on the Peruvian coast to the charming villages of the English countryside. Chloe specializes in showcasing all the must-see attractions on your travel wish list. She lives by the belief that every adventure is a story worth sharing.

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