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Our Favorite Fall Date Night Spots (With a Twist) in the Midwest
Food + Drink • Explore • Things to Do • Chicago

Our Favorite Fall Date Night Spots (With a Twist) in the Midwest

When traveling with my significant other, we always do our best to find a unique way to enjoy a traditional “date night” at our vacation destination – no matter where in the world we happen to be. This helps us appreciate the day’s discoveries, remember our favorite parts of the vacation and really decompress after a long flight or a full day exploring.

A Piece Of Cake Sitting On Top Of A Wooden Table

If you want in on this lovely plan for your own travels this autumn, you may just fall for one of our top spots for a fun date night in Chicago and Minneapolis.

First up, the Windy City. Whether you’re staying at our Loews Chicago Hotel (located in downtown Chicago’s Streeterville neighborhood) or our Loews O’Hare Hotel (located conveniently near O’Hare International Airport), you'll be well placed to enjoy one of these unique date-night ideas.

Chicago O'Hare

The Museum Of Hummels may not be the first idea that comes to mind when you think date-night location, but hear us out. This tribute to the Hummel — keepsakes that look similar to those Precious Moments porcelain figures your grandma no doubt adored — is located in an inconspicuous strip-mall on Higgins Road in Rosemont, IL, not far from Chicago O'Hare. Taking a meander through the museum to check out over 1,000 rare Hummels and wood carvings can be a lot of fun, making you feel like you're on an episode of TV's Antique Road Show as you play guessing games on how much each collectible costs.

A Man Standing On A Stage

Photo credit: philonsax

Staying with us at our Loews O’Hare property and want to catch some of the famous toe-tapping jazz Chicago is known for? Look no further than our very own Montrose Room, where we host a rotating selection of local jazz musicians for a lively yet intimate date night – just steps from your guestroom door! Be sure to purchase your ticket before arriving by clicking here.

Chicago Downtown

A Green Plant In A Garden

Downtown has a plethora of date-night options that are not only unique but cost-effective.  Like warming up on a cool fall day at Lincoln Park Conservatory. Open year-round, this tropical oasis is full of exotic plants from around the world. Stroll the stone pathway from room to room and get up close with species of plants you would only otherwise see on the Travel Channel.

Next, light up the night at Art on theMART along the Chicago River. Grab a couple of cups of your favorite hot beverage and head on down the Chicago Riverwalk to catch the world’s largest digital art instillation featuring a rotation of work by local and international artists.

To cap things off, star-gaze after-hours at the Adler Planetarium’s Adler After Dark 21-and-over-only monthly event. Each evening boasts a different theme, so you may experience a tribute to the Star Wars films or perhaps a planetary prom. You'll have access to explore the exhibits, see unlimited shows in the museum’s theaters, take in special programming and drink cocktails in the lobby.


A Large Tall Tower With A Clock At The Top Of A Building

For something a little different in Minneapolis, why not explore the city's history on your date? A visit to Mill City Museum will give you an intimate view of the one-time flour mill's colorful past. Take a ride up the glass-enclosed elevator to explore the remains of the historic landmark and enjoy stunning views of the local landscape.

A Cup Of Coffee On A Table

End the evening with a nightcap crafted by... you. Build you own Old Fashioned at Apothecary Bar & Lounge located off the lobby of Loews Minneapolis Hotel.

As you belly up to the bar, ask the bartender for their B.Y.O.O.F menu – this cute notecard boasts dozens of options so you can curate your own concoction. The best part? They’ll save your custom recipe for your next visit – so you can recapture the magic of this date night on the next one.