Last Updated On: January 29, 2018

Valentine’s Day is just around the corner and you just might want to plan something a little special for your sweetheart. How about Chicago staycation? I have enjoyed staycations in Chicago many times and I have to say I really love them. It’s nice to feel a little fancy and stay downtown in a luxury hotel. Order room service or get dressed up and go out somewhere fun for dinner. Enjoy drinks in the hotel bar before bed. Sleep in or enjoy a delicious breakfast.

Sounds kinda great, doesn’t it?

So, I did a little research for you and found the best hotel deals right now in Chicago to enjoy a little staycation. If you are interested I would book soon so you can get the best deal.

Best hotel deals in Chicago

The best staycation hotel deals in Chicago

Virgin Hotels Chicago – rates from $179

Staycation deal includes:

  • French Macaroons
  • Split of Champagne
  • Complimentary late check-out

The Drake Hotel – rates from $150

Staycation deal includes:

  • Welcome Mug(s) filled with coffee or Hot Chocolate
  • Complimentary Self-Parking for one vehicle
  • Skate Rental for two at Millennium Park Ice Rink
  • Complimentary in-room Premium Wi-Fi

Loews Hotel Chicago – rates from $189

Staycation deal includes:

  • Overnight accommodation
  • Valet parking for one vehicle
  • 20% off at ETA Restaurant + Bar and Spa at Loews Chicago. (Spa reservations are required.) 
  • Hot chocolate
  • Cookies with recipe by Pastry Chef Aaron Manuyag
  • In-room movie credit (up to $19.99)

Four Seasons Chicago – rates from $375

Staycation deal includes:

  • A bottle of Moët & Chandon
  • A sweet treat

Omni Chicago Hotel – rates from $199

Staycation deal includes:

  • Luxurious accommodations
  • Concierge pre-call to assist with special romantic requests
  • Two Mini-Bottles of Moet & Chandon Rose Champagne and Chocolate Covered Strawberries (3) delivered to room upon arrival
  • Standard “romantic” turndown with robes, music, and lighting
  • Late check-out, 1 p.m.

Best hotel deals in Chicago

Swissotel Chicago – rates from $185

Staycation deal includes:

  • Signature chocolate-dipped strawberries in your room
  • Champagne toast for two in Amuse
  • Buffet breakfast for two in Geneva Restaurant
  • 2 p.m. late checkout

Thompson Hotel Chicago – rates from $379

Staycation deal includes:

  • Booking for two in a 90-minute bath experience at Chicago’s newest luxury spa, AIRE Ancient Baths
  • Receive a welcome amenity of prosecco and chocolates in the evening
  • A late check out of 2 p.m.

Viceroy Chicago – rates from $250

Staycation deal includes:

  • Early check-in based on availability
  • Luxurious accommodations in a Viceroy guestroom
  • Half bottle Champagne upon arrival
  • Special sweet treat from our friends at Sugarfina
  • Breakfast for two in Somerset restaurant
  • Late check-out at 2 p.m.

Ambassador Chicago – rates from $145

Staycation deal includes:

  • Receive a daily $25 food and beverage credit
  • Complimentary valet parking
  • Two complimentary drink vouchers

The Peninsula Chicago – rates from $399

Staycation deal includes:

  • Complimentary room upgrade to the next category
  • Early check-in and late check-out times
  • Daily American Breakfast for two for guests who reserve a suite
  • Access to Fitness Centre, 30 complimentary weekly fitness classes, and indoor, half-Olympic length swimming pool
  • Bedside charging station for all smartphones
  • In-room Nespresso machine
  • Access to our “Keys To The City” program, offering exclusive experiences at Chicago’s best attractions
  • Complimentary high-speed Wi-Fi and worldwide VOIP phone calls

Dana Hotel and Spa – rates from $419

Staycation deal includes:

  • Enjoy a $100 dining certificate at the critically acclaimed, Portsmith
  • A 50-minute couples massage by Spa at Dana
  • Special heart-shaped macaroons to share


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Based on the true story of a girl in her twenties who packs her bags and follows her lifelong dream of moving to Chicago. Take a journey with Kelly and discover the hidden gems you never knew about – as she starts a new career, makes new friendships, and even falls into an unexpected romance. Learn more...

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Girl's Guide Chicago