Romantic Valentine’s Day Hotel Packages and Ideas Around Chicago!

Staycation at 21c Museum Hotel Chicago

21c Museum Hotel – Romantic Getaway Package

Enjoy some relaxation and romance with this special package for you and your loved one.

Romantic Getaway Package includes:

  • One (1) bottle of champagne
  • One (1) box of chocolate truffles
  • $50 Lettuce Entertain You restaurant gift card (delivery available)
  • Early check-in and Extended checkout

The Rose Hotel near O’ Hare Airport is offering ‘Room Full of Roses Package’

Treat your sweetie to the ultimate, over-the-top Valentine’s Day experience. Wow them when you open your guest room door to a room completely filled top to bottom with red long-stem roses as well as everything else you need to sweep them off their feet this February  Offer includes:

  • A room filled to the brim with 400 rose
  • Free In Room Dining breakfast for two
  • Welcome amenity and bottle of sparkling wine or cider upon arrival. Late check out


Is offering their ‘SO- IN LOVE Package’ which includes a two night stay in their deluxe or suite style accommodations, one bottle of Veuve Clicquot, one box of SOPHY Signature Truffles, one $50 credit to their restaurant/bar Mesler, & outdoor skating for two at Midway Plaisance Park with rentals.

Total with room $437 

The Gwen Hotel – Love in the Windy City

Has the ‘Love in The Windy City” package available until Feb 23rd, 2022. It includes Prosecco at Check-in, $50 Daily Dining Credit, and 4PM Late Check-Out. 

Your next date night starts at The Gwen, a Luxury Collection Hotel. Whether you’re a local or just visiting Chicago, there is so much to do in the Windy City with your loved one.

Start your stay off right with a glass of prosecco on arrival before checking-into your luxury accommodations. Next, spend your days lounging in your room or exploring the city. Whichever you choose, make sure to use your daily 50 USD dining credit to enjoy a bite at Upstairs At The Gwen, our rooftop terrace with breathtaking city views, firepits, a delicious menu, and creative craft cocktails or Kostali by Naha, our celebrity-chef-driven concept that pairs exclusive wines with an epicurean tour of the Mediterranean’s best dishes. Finally, end your romantic weekend with a complimentary 4PM late check-out and spend that extra quality time with your loved one before heading home refreshed and reconnected. 

Total is around $330 

Breakfast in bed at Fairmont Hotel

Fairmont Chicago

No need to choose. You can have it all on your romantic getaway: dine out, see a show, unwind with a massage for two and watch the city lights come up from your room with a view. Fairmont Chicago offers a MySpa Retreat For Two, Intimate In Room Dining & Date Night Concierge. 

Our knowledgeable concierge team knows the Windy City inside and out. Tell us what you have in mind, and we’ll plan every detail, make reservations, book tickets and get you VIP access to Chicago’s best restaurants, festivals, concerts, shows and tours. Or ask about our special packages.

Our Art Institute Package gives you a private behind-the-scenes tour of The Art Institute of Chicago, with extras such as complimentary valet parking, chilled Veuve Cliquot Champagne and Fairmont Gold privileges, or even an exclusive after-hours tour with the curator for you alone.

Staypineapple – Celebrate Good Times

Celebrate good times with sparkling wine, truffles and free parking*

  • Bottle of Sparkling Wine – a little bubbly on ice is always nice.
  • Artisan Truffles – a box of 4 decadent chocolates.
  • Free Parking* – save some $ to splurge on your favorite takeout!

Kimpton Gray – Discounts

Upgrade your Valentine’s Day with discounts on spa suites, plus in-room massages.

Hotel Zachary – Love Alma Package

This Valentine’s Day, we invite you to write

your own love story with a special stay at Hotel Zachary. Our “Love, Alma” package, named for Zachary Taylor Davis’ wife and long-time muse, Alma, includes:

  • Two Hotel Zachary Robes to keep
  • Chocolate Covered Strawberries
  • Bottle of Champagne on ice
  • Late checkout the following day (noon)

Guests can choose from a variety of king and suite rooms for the special. Rates apply for reservations from February 11-14, 2022; some restrictions apply.

Celebrate Romance at The Peninsula

Experience a romantic escape at The Peninsula Chicago, recently named Chicago’s “Most Romantic Hotel” by USA Today. Reserve our Celebrate Romance package with an overnight stay in a suite and allow us to make you and your loved one feel special.

Exclusive benefits:

Suite of choice at the Best Available Rate, pending availability. Complimentary daily American breakfast for two, In-room welcome bottle of Champagne, In-room rose petals during turndown service

Complimentary benefits:

Access to Fitness Center, complimentary weekly fitness classes and an indoor, half-Olympic length swimming pool

  • Bedside charging station for all smartphones
  • In-room Nespresso machine
  • Complimentary high-speed Wi-Fi and worldwide VOIP phone calls
  • Local phone calls
  • Local daily newspaper

Validity: Offer valid for suite reservations from February 11 – 14, 2022

Suite Life at Lincoln

Book a two-night stay in one of our Junior or Lake View suites and receive 20% off our Best Available Rate, plus a few special perks.

Package Includes:

  • Late checkout at 1pm
  • A bottle of bubbly at check-in
  • Waived amenity fee


Treat Your Sweetie with Our Picks for the Best Valentine’s Day

This Valentine’s Day, hit the escape button to The Magnificent Mile location of The Drake Hotel for a romantic overnight stay between you and your better half with the added assurance of Hilton CleanStay.


Why not indulge a little in the name of love? Be Swept Away with a Wink & a Kiss guaranteed to mark the start of a memorable staycation and relaxing way to spend Cupid’s holiday with the one you love.

Package Inclusions:

  • Overnight accommodations for two
  • Dessert for two at Coq d’Or
  • Champagne and macaroon takeaway from Lavazza
  • Early check-in and late check-out, based upon availability
Sipping Champagne at Viceroy Chicago

DATE NIGHT IN – $50 F&B CREDIT & MORE at Viceroy Chicago

Your perfect “night in” is waiting at Viceroy Chicago. Treat your sweetheart to an evening of comfy-cozy luxury — we’ll bring everything to you. Order from our in-room dining menu, cue up a movie, and snack on some popcorn. While everything is ideal inside, the architecturally notable Gold Coast neighborhood is right outside our door, should you want to sneak out for an evening stroll.

Offer includes:

  • $50 food and beverage credit
  • Unlimited movies
  • Popcorn delivered to your room
  • 2:00 PM late check-out

Plus, consider making reservations for a St. Valentine Chalet (greenhouse)  at Devereaux Rooftop (located on their rooftop)

Rendezvous For Two ROMANTIC RETREAT at DeerPath Inn

Experience the perfect romantic retreat with a winter getaway in Lake Forest. Enjoy a luxurious suite for two, breakfast in bed and more!

Package Includes:

  • In-room, romance-themed Afternoon Tea Service
  • Romance-themed welcome cocktail upon arrival.
  • Complimentary bottle of wine to be enjoyed in-room.
  • In-room breakfast provided each morning.
  • Rose petal turndown is available upon request.

Guests can call the hotel directly to check on availability and make reservations, 847-234-2280.

Stay & Dine at Chicago Athletic Hotel

Enjoy a dining credit on us for up to $100 based on your length of stay! Valid at Cindy’s, Cherry Circle Room, Game Room, Drawing Room and In-Room Dining. Please note, some restaurants require reservation.

Milk Room Chicago

**Ryan and I HIGHLY recommend checking out the Milk Room there. It’s a super exclusive (8 seat) bar that serves up cocktails made with rare spirits & ingredients!

Write Your Love Story Romance Package – Hotel Arista

It’s your own Once upon a time…. Begin telling your story of romance with an evening of luxurious accommodations with a bottle of bubbly and rose petals.

Package Includes: 

  • Overnight Accommodations
  • Bottle of Sparking Wine
  • Rose Petals (placed on bed)

Romance & Indulge Couple’s Package – Hotel Arista

All the luxury you can handle at our Four Diamond accommodations with a $100 indulgence credit towards dinner, spa or breakfast, plus rose petals and a bottle of bubbly.

Romance Package – Harvey House B&B

Bubbly & Truffles – A bottle of chilled sparkling wine paired with a box of 4 truffles. These exquisite chocolates are locally sourced hand-made Ethereal Craft Chocolates. $40 add-on

Treat Her or Treat Him – Vroom Mansion

Our most popular package makes for a wonderful surprise upon arrival. With all of her favorites, this package is a way to show how much you really care.

This package is completely customizable. Surprise her with:

  • Her favorite flowers
  • A restaurant gift certificate
  • Indulgent sweets such as truffles, chocolate-covered strawberries, or a gourmet cake paired with a beautiful fruit, cheese, & cracker dish
  • Her favorite wine, champagne, or sparkling grape juice

$110 Add-on

Treat Him

Want to do something special for him? Show the man in your life that romantic getaways can be just as enjoyable for him! Customize this package with:

  • His favorite six-pack or bottle of wine
  • A gift certificate to a nearby sports bar or restaurant 
  • Manly munchies, such as chips & salsa, beer nuts, and more
  • His favorite sweet treat: cookies, cake, or brownies
  • A tasty cheese and cracker pairing

Magnifique Romance – Sofitel Mag Mile

Available from 8 January 2021 until 17 February 2021

Rediscover romance at Sofitel Chicago Magnificent Mile with our elegantly styled Romance Package. This memorable package includes amenities that will enhance your special stay from beginning to end.

  • Luxurious comfort in elegantly styled accommodations
  • A bottle of champagne on ice delivered to sip any time you wish once during your stay
  • A romantic welcome amenity
  • A complimentary full American breakfast for two from CDA takeaway
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