Chicago In Style

In Advice and Tips, Chicago, Destinations, Luxury Travel, USA

If your want to take your next trip to Chicago in Style the below list of hotels, spas, shopping excursions, restaurants, and must-see attractions will help you to plan the perfect itinerary.


Chicago is the home of many notable hotels. Each of the hotels below is more than a hotel—they are rich in history yet timeless and feature some of Chicago’s top rated restaurants and spas.


The Drake Hotel

The Drake is located on the north end of Chicago’s infamous Magnificent Mile. This 1920’s hotel is the home of some of Chicago favorite restaurants such as The Cape Cod Room and The Palm Court which hosts traditional Afternoon English Tea and evening events. The Drake is in walking distance to the infamous Oak Street shopping area and offers its guest packages with spa treatments, shopping excursions, and much more.


Palmer House

This is another of the historic Chicago hotels located in downtown Chicago. This hotel has been in Chicago’s South Loop, just off of Michigan Avenue, since 1871. It places you close to Millennium Park, The Museum Campus of Chicago, the Theater District, and State Street shopping. The Palmer House also has their own in-house spa and is surrounded by a large variety of restaurants.


The Peninsula

The Peninsula was designed to bring traditional Hong Kong hospitality to Chicago. This hotel was voted the “#1 Large City Hotel in the US and Canada” by Travel & Leisure magazine. It is home of the Zagat rated #1 Chinese restaurant in the Chicago, Shanghai Terrace. You can also dine in their European restaurant and wine bar, American dining, outdoor restaurant The Terrace which specializes in small plates, and you can enjoy their Chocolate Bar every Friday and Saturday evening in The Lobby restaurant. They also have their own in house full service spa.


Sofitel Chicago

This French inspired glass hotel is just a short walk from Michigan Avenue. It features modern décor and has a French fusion restaurant Café des Architectes.  While this hotel does not have an in-house spa it places you within walking distance to multiple Chicago spas.

Other notable Chicago hotels are Millennium Knickbocker, The Wit, W Hotel, Congress Plaza, and the Renaissance Blackstone



Many of the above hotels have top notch luxury spas that will not require you to leave the comfort of your hotel. If you would like a selection of additional Chicago Spas consider the below selections.

  • Mario Tricoci
  • Spa Nordstrom
  • Elizabeth Arden Red Door Spa
  • Eshé Day Spa and Salon



Magnificent Mile

You can’t do Chicago in Style without experiencing the Magnificent Mile. This 13 block strip is jammed packed with over 400 stores, boutiques, and high-end designers—Chanel, Ralph Lauren, Top Shop, La Perla, Armani, Prada, Lois Vuitton, Saks, Macy’s, Bloomingdales, Niemen Marcus, Tiffany’s, Cartier, Rolex, and many more.

Oak Street

Just off of the north end of the Magnificent Mile is another stretch of high end stores and specialty shops such as Barneys, Agent Provocateur, Harry Winston,David Yurman, GRAFF, and local Chicago designers.

If boutiques are more up your alley head to the South Loop which is full of independent retailers and the home of Chicago’s infamous Jewelry district.  You can also take a stroll in the Wicker Park and Bucktown neighborhoods for more small boutiques and local designers. Some of Chicago’s most notable designers are Borris J Powell, Lara Miller, Elise Bergman, Maria Pinto, and Bryan K Osburn. These designers are in demand and are available by appointment only. Some of these designers’ pieces can be found in boutiques throughout Chicago.



In the hotel section above we mentioned some of Chicago’s top pick for Restaurants. Below is a list of a few more you may want to try to squeeze into your itinerary.

Signature Room

This restaurant is on the 95th floor of the John Hancock building which gives its guests a 360 degree view of the city. Even the view from the powder room is breathtaking.

The Girl and the Goat

This is Top Chef winner Stephanie Izard’s famed restaurant. Her restaurant showcases her masterful skills and leaves no question as to why she was the Top Chef winner.

The Walnut Room

The Walnut Room is wonderful all year round, but is a must-see during the holiday season. Their holiday décor and menu is a long standing Chicago attraction, meaning reservations during late Nov-Dec need to be booked at least 6 months in advance.

The Park Grill

This restaurant sits in the spectacular Millennium Park directly under Clouds Gate or the “silver bean” as it is referred to by many. If you dine at Park Grill during the spring or summer take a stroll through the parks Lurie Gardens after you dine or in the winter you can go ice skating in the park.

Table 52

You can’t talk about food in Chicago without mentioning famous chef Art Smith. His famed restaurant turns southern foods into delicious delicacies.  Seats here are hard to come by so make your reservations in advance.


Moto is your pick if you are looking for a one of a kind dining experience. Moto offers an artful tasting menu where the chef selects your courses for the evening.  You can choose from 5, 10, or 20 course meals that take up to 5 hours to complete. All tastings can be arranged with wine pairings or you can order from one of their many specialty cocktails.

Dinner Cruises

For a bit of romance head to Navy Pier and take a dinner cruise around Lake Michigan. If you are in Chicago between Memorial Day and Labor Day book your dinner cruise on Wednesday or Saturday night so that you can view the Navy Pier fireworks show from the cruise.


Casual Classic Chicago Dinning

If you want to sneak in some traditional Chicago casual dining while in town head to Portillo’s, Giordano’s, Lou Malnati’s, Piazano’s, Hot Doug’s (be prepared to stand in line for 45min-1hr), China Town, Little Italy, Garrets Popcorn, or Terry’s Toffee.

Arts & Entertainment

The entertainment and arts selections are limitless in Chicago. It’s not likely that you will have time for all of the entertainment below so select your preference of these notable selections.

Live Performance

Live performance options are unlimited while you are in Chicago—Broadway shows, test runs of Broadway shows before they head to New York, musicals, plays, opera, symphony, Blue Man Group, Second City, Improv Olympic, The Joffrey Ballet, Hubbard Street dance, live Jazz and Blues and multiple touring shows from around the world.


Chicago is known for being the original home of the sky scraper and has buildings designed by several famous Architects such as John Lloyd Wright, Mies van der Rohe, and William W. Boyington.  You can enjoy a selection of architectural day tours from The Chicago Architecture Foundation. The most popular is the river boat tour that lets you view the city from the Chicago River while relaxing with a glass of wine.


Chicago has many notable museums and cultural attractions. Be sure to stop by the Museum of Contemporary Art (MCA), The Art Institute, check the listing of events at the Chicago Cultural Center, and The Bahia Temple in nearby Wilmette,

Carriage Ride

Nothing says Chicago like heading to the Water Tower and taking a carriage ride through the city.

The above hotels and attractions give you a multitude of selections to plan your next trip to Chicago in style!