$139 – Chicago: Summer Stays at Historic Hotel near Mag Mile

Millennium Knickerbocker Chicago
Alice Wu
Deal Expert

The Deal

TOP 20 - Sells out quickly! Book by June 28

Steeped in history, this Chicago landmark has hosted presidents, Al Capone and Playboy Bunnies. Modern-day guests can save over 25% on summer stays just a block from Michigan Avenue.

  • Standard King rooms start from $139
  • Select weekend stays are just $30-$60 more
  • Parking is available for an additional $40 (reg. $67). The parking option is limited on Friday-Saturday stays, so be sure to book early.

"Luxury here extends to the service" -- Fodor's

Why We Love It

  • Half a block from Michigan Avenue and a mile from Navy Pier
  • A dazzling 90-year history, including as a former Al Capone hangout and as the Playboy Towers
  • Find some shoreline in the Midwest: the Oak Street Beach is about two blocks away
  • The lobby ballroom maintains a splendid, jazz-age grandeur


From lobby to penthouse, the Millennium Knickerbocker Chicago hotel is steeped in history. The lobby maintains its original 1927 opulence, with double-height ceilings, arched windows and wrought-iron balconies. Sneak a peek at the crystal ballroom, a splendid, barrel-vaulted hall dripping with gilding and crystal chandeliers. Another oak-paneled banquet hall on the 14th floor used to be a casino reputedly run by Al Capone's brother, and frequented enough by the mobster to require a secret escape stairwell to the street.

The smallish rooms are clean and contemporary, and bathrooms are marble-tiled with handheld showerheads. Guests interested in the hotel's lurid history -- which includes a stint in the 1970s as Hugh Hefner's Playboy Tower -- can take one of the property's weekly tours.

The hotel is just around the corner from Michigan Avenue, which has some of the city's best shops. In a city known for architecture, some of the top landmarks are right here, including the art deco Palmolive Building next door. At the end of the street against the lakefront are Ludwig Mies van der Rohe's midcentury masterpiece apartments. The hulking crossbeams of the John Hancock building reach toward the clouds one block over.

From the press:
  • "Perfect for visiting many of downtown's most popular tourist destinations" -- Gayot
  • "Formerly Hugh Hefner’s swinging Playboy Towers, this regal property now caters to a more refined crowd" -- Time Out Chicago



  • Bar
  • Newspaper / magazines
  • Fitness classes
  • Gym / fitness center
  • Restaurant
  • No pets allowed


  • 24-hour front desk
  • Baby-sitting service on request
  • Concierge service
  • Currency exchange / ATM
  • Express check-in / checkout
  • Laundry / dry cleaning
  • Business center

Room amenities

  • Air-conditioning
  • Central heating
  • Coffee / tea-making facilities
  • Iron and ironing board
  • Mini bar
  • Pay-per-view / movies on demand
  • Safe
  • Sitting area
  • Flatscreen TV


  • Complimentary Wi-Fi in public areas
  • Internet access (fees apply)
  • High-Speed Wi-Fi (fees apply)


  • Bathrobes
  • Hair-dryer
  • Luxury toiletries

Parking Valet Parking is $65 per night + tax.  Charges will be added to your bill on checkout.
Prices are subject to change by the hotel.

  • Valet service (fees apply)


  • Accessible bathroom in some rooms
  • ADA compliant rooms
  • Facilities for guests with special needs
  • Roll-in shower
  • Wheelchair accessible

Please note: Some amenities may not be available in all rooms and some amenities or services incur an additional charge and are subject to change. Please check with the hotel directly.


Check-in: Standard check-in time: 3pm. Minimum age required to check in: 21.

Checkout: Standard checkout time: 12pm.

Children and additional guests: Children 17 and under stay free of charge when sharing parents’ room and using existing bedding (on request). Crib available on request and in the Standard, Superiors and Suites only; free of charge for children under 4. Extra bed available on request and in the Superiors and Suites only: $20 per night + tax for children and adults.

Pets: No pets allowed.

Cancellation: Cancellation policy & booking conditions vary by 'rate plan'. These will be displayed on the payment page after you have searched for your dates and selected a rate.

Save over 25%

$139 / night


When You Can Go

Sunday-Thursday in July-August; weekends are +$30-$60

94% (68 Member Ratings)

"Lots of charm but functional for business as well"
May 19, 2017
Indianapolis, IN, United States

Getting There

It's 30-40 minutes by taxi from Chicago O’Hare International Airport to the hotel, though the trip will take longer at peak times. Public transportation from O’Hare is available via the El Blue and Red lines. Transfer from the Blue line to the Red line at Lake and get off at the Chicago Red line stop, about seven blocks from the hotel. The trip takes a little over an hour.

Have a Question? Contact Travelzoo.

Customer Service available 24 hours

Rates may vary by date, are subject to availability and are not guaranteed until your purchase is complete.

The room rates listed are for double occupancy per room unless otherwise stated and exclude tax recovery charges and service fees.

It is the responsibility of the hotel chain and/or the individual property to ensure the accuracy of the photos displayed. Travelzoo is not responsible for any inaccuracies in the photos.

94% Positive
(68 Member Reviews)
Ratings & reviews reflect verified member feedback for Millennium Knickerbocker Hotel over the past 15 months.
4.4 Ambiance
4.8 Location
4.3 Rooms
4.6 Quality of Service
4.6 Value for the Money
Show Reviews
Enjoyed Most
Lots of charm but functional for business as well
Scott May 19, 2017 Indianapolis, IN, United States
Enjoyed Most
Vercammen beautiful clean rooms and premises
Scott Mar 15, 2017 Lake Villa, IL, United States
Enjoyed Most
the room size was great
Other Comments
something went terribly wrong. A manager was supposed to get back to me and never did.
Tamar Feb 28, 2017 Saint Louis, MO, United States
Enjoyed Most
I purchased this Travelzoo coupon for my son and wife as a Christmas present. I put the purchase on my credit card. When my son and wife were checking out on the next day they were told the card merely held the room for them. They had to pay for the room. I was not happy at all that I was not told that my card was not actually paying for their stay. It ruined a Christmas gift because they had to pay for the room on their credit card. I have purchased many Travelzoo hotel stays and have never had this problem! I would not purchase another coupon at your hotel.
Edward Feb 21, 2017 Libertyville, IL, United States
Enjoyed Most
Other Comments
Great hotel!
Manuela Feb 06, 2017 chesterfield, MO, United States
Enjoyed Most
Other Comments
Modern amenities
Iskandar Feb 04, 2017 Mount prospect , IL, United States
Enjoyed Most
Very friendly valet. Helpful front desk.
James Jan 29, 2017 Irving, TX, United States
Enjoyed Most
Deal was for a king bed but we got 2 full beds. I went with my daughter. Room was clean, modern and quiet.
Diane Jan 23, 2017 minster, OH, United States
Enjoyed Most
Price and location
Other Comments
Very clean and modern rooms
Renee Jan 23, 2017 Greenfield, WI, United States
Enjoyed Most
Staff and location very nice
Other Comments
Very small rooms despite upgraded to jr suite, broken hairdrier, room so hot even after lower thermostat. Had to open window and ask for fan. Bed/pillows very uncomfortable. Will stay somewhere else next time.
lisa Jan 23, 2017 tinley park, IL, United States

More Great Deals & Tips

$139 – Chicago: Summer Stays at Historic Hotel near Mag Mile

Save over 25%

$139 / night