BOUTIQUE HOTELS IN CHICAGO'S PREMIER NEIGHBORHOODS
Chicago’s Best All-In Hotel Value
Breakfast for two, two cocktails nightly, dinner & spa credits—all included, with every stay upgrade.
Worth over $200 per night at other downtown hotels.
9 years in a row!
Chicago voted Best Big City in the U.S.
Locations
Book Direct For Best Rates + Perks
Welcome to an Exceptional Stay
We’re delighted to welcome you. At our hotel, we do things differently — and better. While your total cost includes a base rate and a $25 Reservation Services/room/night plus, THE PRIVATE GUEST CLUB® Upgrade Best Value Package ($59.95 or $79.95 applies to all reservations made on 1-12-26 or later), you’ll find that the all-in price is equal to or less than other comparable hotels in downtown Chicago.
THE PRIVATE GUEST CLUB® Upgrade Best Value includes:
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Daily Breakfast for Two (a $70 value)*
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Two Complimentary Cocktails per Night (a $34 value)*
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Nightly Dinner Credit ($10 value)
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$50 Credit at Skin Bar and Studio Medical Spa
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Early Check-In & Late Check-Out (up to $50 value)
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$25 Off your next Direct Booking at any of our hotels
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4-Bottles of Spring Water Daily ($15 value)
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High Speed WiFi Access
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Morning Coffee & Tea Station
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24/7 Access to the Full Gym On-Site*
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Rooftop Terrace/Deck*
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Live Music and/or DJ on Weekends*
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Exclusive Local and Worldwide Perks available only to our guests
*Only at Ambassador & Mag Mile Location
Total Package Value over $250!
No other hotel in the city offers this level of value, and all of it is fully disclosed during the booking process — there are no hidden fees, only exceptional benefits.
We believe you deserve more than just a room — you deserve an experience.
Note: The $59.95 or $79.95 per room, per night Upgrade Best Value Package is available to all reservations made on 1-12-26 or later, Private Guest Club® package plus the $25 per room, per night Reservation Services applies to select bookings and is either included in the rate at time of booking or payable at check-in, that includes daily food and beverage credits along with exclusive guest experiences and perks.
Click Here to view all benefits or Here to read the full terms & conditions.
book direct & unlock exceptional benefits with the guestbook
When you book directly through The Chicago Hotel Collection, you unlock exclusive deals and gain access to The Guestbook—a rewards program designed to make your stay even more rewarding.
Here’s why booking direct is your smartest choice:
best available rates
Always get the lowest rates you’ll find anywhere—guaranteed.
exclusive member deals
Enjoy perks, discounts, and offers you won’t find on other booking sites.
cash rewards
Earn up to 15% back on your stay as cash, travel credit, or charitable donations.
How it works:
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Sign up to access Member Exclusive Rates on any Chicago Hotel Collection property’s direct booking site.
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Choose your dates and room type, then join The Guestbook for free at checkout—it only takes seconds!
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Start saving, earning, and redeeming rewards immediately.
Don't settle for less—book direct and enjoy the ultimate combination of value, savings, and perks!
Learn More about The Guestbook here. Any inquiries about cash back offer redemption after stay should be directed to The Guestbook.
Après-Ski Opry: The 29th Floor Experience
📍 The 29th Floor Rooftop Lounge & Deck
at The Chicago Hotel Collection – Magnificent Mile
⚠️ Capacity strictly limited to 100 guests
🎟️One lucky guest holder will win a complimentary night stay in a suite at The Chicago Hotel Collection.
We’re transforming our 29th-floor rooftop into a full-scale Après-Ski Opry experience—a one-night-only winter takeover inspired by alpine ski lodges, Nashville Opry flair, and elevated Chicago nightlife.
EVENT FEATURES:
🎿 29th-Floor Rooftop Après-Ski Takeover
🎶 6 Featured DJs
❄️ 2 Heated Outdoor Rooftop Igloos - RSVP
🍾 VIP Bottle Service Experiences - Limited Space
🔥 Fire pits & winter lounge vibes
🍢 Fire pit S'mores stations upon request
🍱 Passed Appetizers (7pm-9pm)
🍸 Full-service bar + signature cocktails
🍽 Full dinner & late night menu available
🏔 Two guest rooms transformed into pop-up après bars and activations
📸 Immersive photo moments & professional photography
🎟️ One lucky guest holder will win a complimentary night stay at The Chicago Hotel Collection.
⚠️ Strictly limited capacity: 100 Guests.
LOVE SUCKS! 💔
(But This Party Absolutely Doesn’t.)
This Valentine’s Day, forget the cheesy romance and step into Love Sucks—a high-energy, unapologetically fun night at the iconic Ambassador Room. Designed for the heartbroken, the happily single, and everyone exhausted by Chicago’s dating scene, this is where sharp style, strong drinks, and great music collide.
No pressure. No pretending. Just a night that hits different.
Why you need a ticket:
🍸 Espresso Martini Pop-Up Bar with customizable foam prints (exes welcome)
🔥 Themed Cocktails like Hot Mess Express & Anti-Love Potion
🥂 1 Welcome Drink to start the night right
🍴 Complimentary Passed Apps throughout the evening
📸 Photo Ops & Themed Décor made for memories (and stories)
🖤 Elegant & Dapper Crowd in a stunning Gold Coast setting
💎 VIP Tables + Bottle Service for groups who prefer premium vibes
🏨 Hotel Stay Giveaway—one lucky guest wins a free night at the
Ambassador
📅 Saturday, February 14, 2026
⏰ 8PM – 3AM
📍 The Ambassador Gold Coast | 21+ Event
Love may suck… but missing this would be worse. 🎟️
Host an Unforgettable Event at The Ambassador
Host your next corporate gathering or special occasion in a setting that has defined Chicago sophistication for nearly a century. Located in the heart of the Gold Coast, the Ambassador Gold Coast seamlessly blends iconic history with modern luxury. Since 1926, legendary figures such as Marilyn Monroe and Frank Sinatra have passed through our doors—setting the stage for moments that endure.
Today, that legacy continues with more than 10,000 square feet of flexible event space, breathtaking rooftop views, beautifully preserved historic venues, and attentive, personalized service. Whether you’re planning an executive meeting, gala, or milestone celebration, an event at the Ambassador Gold Coast is more than an occasion—it’s an experience woven into Chicago’s storied past.
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