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Chicago Luxury hotels

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Chicago Luxury Hotels Guide

Chicago, Illinois, offers much in the way of history and adventure. If you are planning a trip to the Windy City and want to enjoy your stay in style and comfort, Orbitz offers some of the best deals on Chicago luxury hotels that you’ll find.

Between sightseeing and dining out in busy and beautiful Chicago, you’ll want to spend some time relaxing and enjoying your hotel. Luxury hotels in Chicago offer the best in the way of amenities, including fitness centers, swimming pools, complimentary wireless Internet access and local telephone calls, holiday activities, and more. After a long day of exploring the shops and boutiques along Chicago’s Magnificent Mile, enjoy a night in. Settle into your hotel room and enjoy room service and a selection of movies right from your dream bed that’s dressed in soft satin sheets, piled in plump pillows, and topped with a cozy down-filled comforter. If you’re in the mood for socializing and want to enjoy all your luxury hotel in Chicago has to offer, take your party down to your hotel’s lounge and enjoy a complimentary beverage and snacks in a classy setting before heading out for a spectacular night on the town. Many of Chicago’s luxury hotels are located right downtown, within walking distance of many popular bars and nightclubs, such as Enclave and Manor. After all the fun, you’ll appreciate your hotel’s relaxing ambiance when you return, and you’ll smile when you remember you have a delicious breakfast to look forward to in the morning.

If you’ve gathered together a group of friends and are ready to take off for a special week in the Windy City, visit Orbitz for great deals on Chicago luxury hotels, attraction tickets, and much more. With Orbitz as your guide, you’ll be able to find a nice place to stay in Chicago that matches your classy taste and ensures you’ll be set to have fun while you’re there.

Chicago Luxury Hotels

  • Chicago hotels

Featured Chicago Luxury Hotels

From $188

1 The James Chicago

5 stars
4.4 / 5 129 reviews

55 East Ontario Map

Boutique chic luxury in the heart of River NorthUrban professionals feel right at home at the James Hotel Chicago, a shrine to boutique chic style. Every corner pops with stylish details, starting with an illuminated lobby that offers soaring ceilings and 24-hour business center with... More

expensive luxury
great location, extremely clean, and it really feels luxurious. i don't think it's a great value, though, and after accidentally reserving for the wrong day, i felt the staff could have been more...
Aug 5, 2013
Lovely hotel
I recently stayed two nights at the James Hotel Chicago, when in town for a meeting. The hotel is very well situated in the Near North Side area, only a block from Michigan Avenue. The location is...
Aug 29, 2011
From $356

2 The Peninsula Chicago

5 stars
4.8 / 5 49 reviews

108 East Superior Street Map

With The Peninsula Chicago, traditional Asian service is brought to guests in the Windy City. This five-star hotel is located in the heart of the Magnificent Mile; it offers 20 floors of impeccable accommodations and delivers amenities and services of a very high caliber. Bask in the luxury of... More

Classy and Inviting
From the check in experience through housekeeping and room-service, this is a top of the line hotel. The rooms are stylish and contemporary - we had a great view as well. No detail is too small -...
Apr 6, 2012
City Luxury
We lived in Chicago for 15 years, so I'd like to say I know the city pretty well. This is the best hotel in the city. Luxurious hotel, great location in middle of Michigan Avenue, prompt staff, and...
Sep 28, 2011
From $308

3 Waldorf Astoria Chicago

5 stars
4.8 / 5 26 reviews

11 E. Walton Map

Best of Waldorf - Includes hotel credit

Coco Channel style and opulence comes to downtown ChicagoThe appeal of the Waldorf Astoria Chicago Hotel centers on its drive to reinvent luxury and remove the monotony that one has come to expect from supposed luxury hotels. This Gold Coast hotel, on the doorstep of the exclusive shopping... More

Excellent, kid friendly luxury
For only a few more dollars we enjoyed a spacious, luxurious suite during our trip to chicago. Excellent location to shopping and dining, courteous staff, gorgeous amenities... Would definitely...
Oct 20, 2013
First class act
The luxury in this hotel is not just in its decor but the service and amenities. Outstanding! Love this hotel and will be back every year for our anniversary!Great Location, close to our fav...
Jan 3, 2011
From $335

4 Park Hyatt Chicago

5 stars
4.7 / 5 15 reviews

800 North Michigan Ave Map

Includes Full Breakfast for 2 & Free Valet Parking

Luxury and elegance on Chicago’s Gold CoastThe location of the Park Hyatt Chicago in the Magnificent Mile and Gold Coast means that guests are never short of things to do. This award-winning hotel provides visitors with a wide range of amenities and services in a sophisticated and friendly... More

Lovely experience
From the location to the the amenities this hotel was a lovely experience. The moment you arrived it was a warm and welcoming experience. From the ice tea and lemonade in the lounge to the bath...
Jul 7, 2014
Great Locations and Amenities!
This was a great hotel, rate, and you are living in luxury! They have a amazing cider mid-day downstairs, a big tub for a bubble bath, and are RIGHT on magnificent mile. I would definitely stay again.
Mar 19, 2013
From $340

5 The Langham Chicago

5 stars
4.9 / 5 9 reviews

330 N. Wabash Ave. Map

Advance Purchase Savings - Save 12%

Conveniently located downtown in a 52-story landmark tower designed by renowned architect Mies van der Rohe, The Langham, Chicago is just minutes away from the boutique-lined boulevards of Chicago's retail hub and within walking distance to many of the city's premier tourist sites. The Langham,... More

Top notch
Wonderful experience. The hotel is expensive, but everything is top -notch. We had a king room, and iit was pure luxury, with huge tv, modern controls for the lighting and a wonderful rain shower....
Aug 25, 2014
Relaxing and extraordinary hotel
This is by far the best hotel that I have ever stayed at. It's in an unassuming building right next to the Trump Tower, but it's really the inside that counts! Excellent amenities - comfortable...
Sep 1, 2014
From $335

6 Ritz-Carlton, a Four Seasons Hotel

5 stars
4.3 / 5 29 reviews

160 East Pearson Street Map

Bird’s eye view of Chicago’s Magnificent MileThe grandeur of the Ritz-Carlton Chicago, a Four Seasons Hotel, is unmistakable in its magnificent setting atop Water Tower Place, overlooking the exclusive North Michigan Avenue. Occupying floors 15 to 30, the hotel boasts 434 guest rooms of five-star... More

Perfect location for everything
The staff was very helpful. Room was perfect for family (executive suite deluxe). The location is in the middle of everything. OR a cab ride away.
Jun 26, 2012
4 Seasons gets more than 4 stars
Great hotel, great staff. Beautiful rooms and worth every penny!
Oct 15, 2014
From $385

7 Four Seasons Chicago

5 stars
4.7 / 5 15 reviews


European style sweeps through this Windy City hotelThe Four Seasons Chicago is mere steps from the city's top attractions including the stylish North Michigan Avenue, Navy Pier and Magnificent Mile. Guests receive five-star service at this landmark hotel, which has recently been re-styled to... More

Wait staff, bartenders left me standing -- ready to order a late dinner -- for 15 minutes. Left the restaurant and ordered room service.
Sep 12, 2014
Great Hotel
Loved the hotel location. I was able to walk everywhere I needed to go. Staff was friendly and helpful. Great hotel stay.
Jun 8, 2014
From $126

8 Warwick Allerton Hotel Chicago

4 stars
4.0 / 5 596 reviews

701 N Michigan Avenue Map

Save 15% on your stay

As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, the Warwick Allerton Hotel Chicago became synonymous with high style, luxurious hotel accommodations and impeccable service. Today, the hotel has kept the commitment to treat every guest like a celebrity and continues... More

Good value
If luxury is what you want, pay twice as much at the other big-name hotels up and down Michigan Avenue. Guest rooms may be small and dècor may outdated, but they are clean and comfortable. For me,...
Jun 26, 2014
Great central location with friendly staff
Great price. Completely remodeled since the last time I stayed here. Excellent central location right on North Michigan Avenue. Nice size king deluxe room. It was right next to elevators, and we...
Mar 27, 2013
From $179

9 The Drake Hotel

4 stars
4.3 / 5 190 reviews

140 East Walton Place Map

Rate includes a $50 USD daily hotel credit

From its beginning on New Year's Eve 1920 to today, The Drake Hotel has defined elegance and hospitality. Set in the prestigious Gold Coast neighborhood at the start of the Magnificent Mile, this iconic Chicago hotel is footsteps from Oak Street Beach and Lake Michigan.Relax at The Drake Hotel in... More

One night stay
Great hotel looks fancy but needs to be updated. Customer service was good
Jul 28, 2014
A Great Chicago Weekend
The Drake provided a perfect home for a weekend of Chicago experiences. Its location is perfect for strolling the Magnificent Mile or enjoying views of Lake Michigan. The Hotel itself was...
Jul 21, 2014
From $159

10 MileNorth, A Chicago Hotel

4 stars
4.2 / 5 407 reviews

166 E Superior Street Map

This boutique property offers a residential-style retreat that soars above Chicago's Magnificent Mile. Each floor is home to no more than 11 spacious guest rooms and suites, and your evenings would be well spent enjoying appetizers and sipping cocktails at the 52Eighty rooftop club. MileNorth?s... More

A Businessperson's Delight!
From the moment I entered the lobby, when a bellhop insisted on taking my bag and the manager upgraded me (at no additional charge) to a high-floor view room, MileNorth exceeded my expectations....
Nov 22, 2013
Excellent location, adequate hotel
Hotel has a terrific location, a block off Michigan Avenue in the heart of the Magnificent Mile, right next door to Gino's East, the best pizza joint in Chicago. That's about the only endorsement...
Oct 12, 2013
From $132

11 Raffaello Hotel

4 stars
4.0 / 5 258 reviews

201 E. Delaware Place Map

Menin Hospitality operates several luxury boutique hotels in Miami and a single hotel in Chicago, the Raffaello Hotel. This cozy boutique hotel is situated right on Michigan Avenue, very close to some of the most celebrated attractions and amenities on the Gold Coast and Magnificent Mile. From... More

Spend the extra dime somewhere else
The check in desk is about 1.5' x 3' with one person. Customer service is not bad but very cold, not at all friendly with the exception of the doormen. The elevators are small, 5 people is packed....
Jul 16, 2014
Wonderful boutique style in the center if everything
My girls and I (12 & 14) stayed here to do some shopping and hit some fancy restaurants. The staff was very friendly and knowledgable. The bakery in the lobby had some incredible homemade donuts....
Mar 27, 2014
From $189

12 Hotel Chicago Downtown, Autograph Collection

4 stars
4.2 / 5 135 reviews

333 North Dearborn Street,(Driveway entrance on 35 Map

Rate Includes Breakfast

Experience the energy and sophistication of the big city when you stay at the Hotel Chicago Downtown, Autograph Collection®. Our boutique hotel is located in the heart of the city's River North area, where the excitement never ends. You'll be minutes away from great attractions, including Navy... More

Enchanting Engagement Weekend
Although the hotel doesn't look like much from the outside, it is very stylish and elegant inside. We loved the decor in the room as well as the large floor to ceiling window with a view of the...
Aug 21, 2013
Great Location, Not So Classy
The room was rather small, but very nice, though i expected it to be fancier or more than standard for a 4 star hotel. Only left 1 glass in the room each day. Standard of 2 would've been nice so we...
Jun 11, 2012
From $159

13 Conrad Chicago

4 stars
4.4 / 5 128 reviews

521 North Rush Street Map

Contemporary luxury on the Magnificent MileThe Conrad Chicago hotel might be a shopper's best-kept secret, like a Chanel bag on sale. Removed from the crowds, the 17-story Conrad maintains a strong city presence with rooms that look out across twinkling lights and landmark buildings. Touches of... More

Sophisticated downtown hotel!
I stayed at the Conrad during the IPW Conference, and really enjoyed it. Wonderful central location, lux accommodations with wonderful staff. Nice lobby with bar and restaurant. Great bathroom with...
Apr 11, 2014
Perfect luxury hotel in perfect location
We came here for a long weekend trip for our anniversary. The room was immaculate and luxurious. We couldn't hear any other guests, only some outside sirens, but that's to be expected in the middle...
May 3, 2010
From $220

14 Sofitel Chicago Water Tower

4 stars
4.6 / 5 131 reviews


Save 25% on your stay

Sofitel Chicago Water Tower provides four-star downtown Chicago hotel accommodations -- minutes from the Magnificent Mile, Navy Pier, the Museum of Contemporary Art, Lake Michigan and upscale boutiques. Designed by the French architect Jean-Paul Viguier, our downtown Chicago Illinois hotel is a... More

anniversary trip
Great experience. Swanky hotel, in my opinion. Everyone was extremely friendly and helpful. Staff offered complementary room upgrade & fridge for our drinks without me even asking. Couldn't ask for...
Aug 12, 2013
Awesome hotel for a romantic weekend
I love this hotel, the location is perfect, the hotel is super clean and swanky, and the rooms are ultra quiet. The bar downstairs is fantastic, hip, modern, and fun. Best of all, the rooms are...
Nov 19, 2012
From $199

15 theWit Chicago - a DoubleTree by Hilton Hotel

4 stars
4.2 / 5 77 reviews

201 N. State Street Map

Signature chocolate chip cookie at check-in

Comfort and convenience in the heart of downtown ChicagoAt theWit Chicago A Doubletree Hotel, guests are provided with comfort, style and luxury in an eco-friendly environment. Offering business and fitness facilities, this boutique hotel is ideal for guests traveling on business or for pleasure.... More

Good value
Good location, very courteous staff. Room and hotel space fine, not luxurious, but clean and safe. Nice restaurant with good food.
Mar 10, 2014
very cool place
Spent the night in a luxury suite and went to roof on the wit for our anniversary, we both loved it!
Jan 5, 2014