Skip Nav
A Home Away From Home

You can pretty much find every type of hotel in Chicago, from traditional luxury to cozy rustic to cutting-edge clean. If you want to steer clear of downtown chains, consider the Casa-approved Longman & Eagle in Logan Square. Set five miles away from the downtown loop, the neighborhood is a mix of old, glorious mansions and bustling boutiques.
Want to stay in the center of things? Casa also likes the James Hotel. Not only is it a hop, skip, and a block from the Magnificent Mile, but it also has an art gallery and spa inside its crisp, modern interior.
Kate Shahl, editor of FreshGuide Chicago, recommends The Elysian Hotel: "The rooms are beyond luxe, with white Carrera marble bathrooms with soaking tubs and beds covered with 460-thread-count Italian linens."

Show Caption +

Dinner can get expensive in Chicago, and thanks to some loophole in liquor laws (probably left over from Prohibition), BYOB is not only socially acceptable, it's encouraged and celebrated — a veritable Chicago thing to do.

Don't just go to any restaurant with a six-pack and a gallon of wine, though! Only certain ones allow it, and FreshGuide Chicago has a comprehensive map of BYOBs across the city. Most tend to be inexpensive joints, but upper-reaching, food-focused ones, like Ruxbin on the edge of Wicker Park and West Town, are popping up around town.

Show Caption +
See an Improv Show

Tina Fey, Stephen Colbert, Jane Lynch, Amy Poehler, I could go on, but it's ridiculous how many famous funny people got their start at Chicago's Second City improv theater. Get tickets to a show, and you might see the next big thing. It's the perfect ending to a Chicago day, and an equally fun way to kick-off the night.

Source: Flickr User saikofish

Show Caption +
A Work of Art and Architecture

With buildings designed by nearly every famous American architect, Chicago is an architectural wonder that favors innovation over tradition. Take your own walking tour or stop in famous buildings, like the Art Institute of Chicago Museum, or see the best view of the city (plus four states) at the John Hancock Observatory.

Source: Flickr User wallyg

Show Caption +
Insider Tip

The final tip is another from FreshGuide Chicago editor Kate Stahl. She loves Chicago to the wind-chilling bone, so we asked her to describe her perfect, romantic night in Chicago right now.

"It would start with a cocktail at The Violet Hour in Wicker Park. Sitting at the bar is a great place to watch the old-school art of mixology, and the drinks are heavenly — just the thing to get you in the mood. Next, I would head to the Gold Coast for dinner at Le Colonial, my favorite date spot. The mood is sexy, the Vietnamese-French food is delicious, and the wine list is both accessible and impressive."

Show Caption +
Next Slideshow Romantic Getaway: Let the Good Times Roll in New Orleans BY Annie Gabillet
Latest Love