Ask Imagine: Romantic Getaway in Chicago

Dear Imagine Lifestyles,

My wife and I are traveling to Chicago for a little weekend getaway. What would be your picks for a romantic hotel and restaurant? Also, what are some activities you could recommend that will be fun for couples to do? Thanks and we’re looking forward to your response!

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Samuel H. – St. Paul, MN



Dear Samuel,

Chicago is the perfect city for your romantic getaway! Imagine Lifestyles Chicago really knows how to plan the perfect weekend trip, one you and your wife will enjoy tremendously. For starters, you should stay at the Peninsula Hotel. We feel it is the most romantic of the hotels on the Mag Mile, and just oozes luxury, comfort, and class. The rich marble and floral décor and millions of fresh flowers really set the stage for romance. The rooms will make you feel like you are on your honeymoon, and the location puts you right in the center of any activity you could imagine. To really make the most of your stay, it helps to fit right in by pulling up in a luxury or exotic rental car. Our Lamborghini Gallardo will let Chicago and your wife know, that you intend on having a very special weekend.

Rosebud on Rush will be the best bet for a deliciously romantic dinner. It is right across the street from your hotel and it Chicago royalty for authentic Italian. The ambiance is dim and cozy and makes you feel like you are in an upscale trattoria on a little side street in Rome. The menu is extensive and offers the best of the best of traditional and rustic Italian fare. My personal recommendations would be to start off with a bottle of Ruffino Reserva Ducale “Gold Label” Chianti Classico; quite possibly one of the best glasses of Italian wine you could drink. Share the Rosebud Chopped Salad, and the Stuffed Mushrooms. Then have either the Cavatelli al Forno or the Rigatoni alla Vodka for your pasta course, followed by any one of the 5 veal dishes. You will NOT be disappointed.

The romance continues with a Chicago Architecture River Tour. This is the most supreme way to not only learn about our magnificent city and it’s history and architecture; but also to spend time with your lovely wife on a romantic river cruise. If you happen to join us in the summer, and you want more privacy; contact Imagine Lifestyles luxury rentals to book a private boat or yacht for a cruise on Lake Michigan. If you don’t happen to have your sea legs, you can always drive all the way up and down scenic Lake Shore Drive in your exotic rental car. There is a set route called the Lake Michigan Circle Tour that will take you north on Lake Shore Drive and follow Sheridan Road all the way up through Chicago’s famous North Shore. The route is gorgeous with views of the Lake and homes that range up to $20 million. Don’t forget to contact Imagine Lifestyles not only for your luxury car rental and luxury boat/yacht rental, but we will also help with all of your luxury concierge needs. We look forward to helping you with your romantic getaway!


Imagine Lifestyles Luxury Rentals


PS While in the city check out our fleet of Chicago exotic rental cars