Trump International Resort & Spa
The five star Trump International Hotel is a luxury accommodation in its own little conclave towering over North Michigan Avenue. From the moment the doorman lets you in to the building you will feel pampered. It’s located along the Riverwalk and just a short stroll from Chicago’s best shopping and attractions.
Nothing says romance like drinks dinner at The Terrace at Trump, especially from May to September when you can watch the fireworks over Navy Pier right from your table. The enormous (23,000 sq. ft.) Spa at Trump is also a perfect place for a couple’s massage, after you relax on the lounges overlooking the Chicago skyline.
401 North Wabash Avenue, Chicago, Illinois 60611
Palmer House Hilton
At the turn of the century, the Palmer House Hilton was a place for performances by legends such as Frank Sinatra and Judy Garland. It also had visitors that included Oscar Wilde and many every U.S. Presidents. The opulence and history is still there, recreated in a $170 million renovation.
Take a historic lunch tour with of the hotel, followed by a drink in the lobby will bring you back to one of the romantic eras of our time. Then, walk to your room hand-in-hand in awe of the pictures of the celebrities and politicians than line the walls on every floor.
17 East Monroe Street Chicago, Illinois 60603
In the River North district of Chicago, the Kinzie Hotel opened in 2014 in the former Amalfi spot as a contemporary boutique offering. It’s surrounded by restaurants and shopping and just a few short blocks from more on Michigan Avenue.
The rooms at The Kinzie are spacious and comfortable for two. The hotel offers a complimentary evening reception in the intimate Double Cross Lounge, as well as breakfast served on each floor of the hotel – so you can bring it back to your room and lull around with breakfast in bed.
20 W Kinzie St. Chicago, Illinois 60654
The Radisson Blu Aqua takes modern to a new level with its chic rooms and common areas, where you can experience breathtaking views of the Chicago Lakefront and Millennium Park. It’s a short walk to the park and many other Windy City attractions.
For your romantic getaway, Radisson Blu offers late check-outs and in-room spa treatments. You’ll also have an indoor pool as well as an outdoor one on the rooftop, where you can order food and cocktails and just enjoy each other’s company.
221 North Columbus Drive, Chicago, Illinois, 60601
In the center of Chicago, The James is another boutique hotel, but it has a flavor all its own. The contemporary design is museum quality, as is the art that is on every wall and table. Attention to unique details in every room is part of the charm of this hotel.
The James offers bikes for you to ride through Chicago’s famous parks, or car service to take you around in the winter months. An intimate dinner at David Burke’s Primehouse is a must. Be sure to order the Cake in a Pan as soon as you sit down so it’s ready for dessert.
55 East Ontario, Chicago, Illinois 60611
Intercontinental Chicago Magnificent Mile
If you want to be in the middle of it all, it doesn’t get much better than the Intercontinental Chicago Magnificent Mile. This hotel has gone through restoration and renovation to keep its early 20th century history, as well as offer modern conveniences.
ENO at the Intercontinental is a perfect date night spot, with flights of wine, cheese and chocolate. If you want to splurge, there’s also Michael Jordan’s Steakhouse. Order their special Garlic Bread to start and then keep your eyes open – the Bulls’ star often makes an appearance.
505 North Michigan Avenue, Chicago, Illinois 60611