Book Chicago Honeymoon Packages

Best Romantic vacations in Chicago

Trump International Hotel & Tower Chicago
The Allegro Royal Sonesta Hotel Chicago Loop
21c Museum Hotel Chicago
Prices and availability subject to change. Additional terms may apply.

Romantic vacation packages for 3 nights

Trump International Hotel & Tower Chicago
21c Museum Hotel Chicago
Fairmont Chicago at Millennium Park
Prices and availability subject to change. Additional terms may apply.

Romantic vacation packages for 4 nights

Pendry Chicago
Palmer House a Hilton Hotel
LondonHouse Chicago, Curio Collection by Hilton
Prices and availability subject to change. Additional terms may apply.

Romantic vacation packages for 5 nights

LondonHouse Chicago, Curio Collection by Hilton
Pendry Chicago
Palmer House a Hilton Hotel
Prices and availability subject to change. Additional terms may apply.

Romantic vacation packages for 6-7 nights

Swissotel - Chicago
Palmer House a Hilton Hotel
The Allegro Royal Sonesta Hotel Chicago Loop
Prices and availability subject to change. Additional terms may apply.

Romantic hotels in Chicago

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Book Chicago romantic vacations

Sparks will fly on your next vacation when you treat yourself and your special someone to the romantic getaway you’ve always wanted. At Chicago, your every wish is taken care of, leaving you plenty of time for long walks and gazing into each other’s eyes. Ditch the dishes and dine out every night; lose the laundry duties and get ready to be lost in the moment. 

Fall in love all over again
It’s time to meet your perfect match—when it comes to vacations, that is. We have all the information you need, right here on Orbitz:

  • Perfect perks: Browse our reviews to find the extras that will make your trip special. Think bottles of champagne, boxes of chocolates and in-room hot tubs. And don’t forget room service, because you’ll never want to leave your suite.
  • Save, your way: You won’t need a trail of rose petals to lead you to amazing deals on Orbitz. Bundle your flight and hotel for extra convenience. Save or splurge, we’ll help you get the best deal at any price point.
  • Make it all-inclusive: Start your relaxation right now. Find Chicago all-inclusive honeymoon packages and leave the details to someone else. Spend your time planning romantic adventures and finding the perfect gift for your sweetie. That’s time well-spent.

Shout your love from the rooftops with Chicago honeymoons and romantic getaways. When you book with Orbitz, you know you’re getting the best for your one-and-only. Get ready to be swept off your feet.

How much does it cost to fly to Chicago?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.