
Chicago Romantic Vacations
Best Chicago Romantic packages

Omni Chicago Hotel
Reviewed on Dec 28, 2024

Hotel Arista
Reviewed on Sep 18, 2024

Sofitel Chicago Magnificent Mile
Reviewed on Dec 20, 2024
3 night Chicago Romantic vacation packages with airfare

The Allegro Royal Sonesta Hotel Chicago Loop
Reviewed on Mar 24, 2025

Sofitel Chicago Magnificent Mile
Reviewed on Dec 20, 2024

Omni Chicago Hotel
Reviewed on Dec 28, 2024
4 night Chicago Romantic vacation packages with flight

InterContinental Chicago Magnificent Mile by IHG
Reviewed on Mar 5, 2025

Fairmont Chicago at Millennium Park
Reviewed on Apr 28, 2025

Virgin Hotels Chicago
Reviewed on Apr 6, 2025
5 night Chicago Romantic vacation packages with airfare included

Hotel Felix River North/Magnificent Mile
Reviewed on Mar 31, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Reviewed on Mar 24, 2025

Swissotel - Chicago
Reviewed on Feb 16, 2025
Romantic vacation packages for 6-7 nights

Swissotel - Chicago
Reviewed on Feb 16, 2025

Pendry Chicago
Reviewed on Jul 5, 2024

Virgin Hotels Chicago
Reviewed on Apr 6, 2025
Romantic hotels in Chicago

The Champagne Lodge & Luxury Suites

LondonHouse Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel
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.
Hotel themes
- Hotels with Air Conditioning in Chicago
- Hotels with WiFi in Chicago
- Kid Friendly Hotels in Chicago
- Hotels with Restaurants in Chicago
- Hotels with Shopping in Chicago
- Business Hotels in Chicago
- Hotels with a Gym in Chicago
- Hotels with Free Parking in Chicago
- Hotels with Bar in Chicago
- Hotels with Free Breakfast in Chicago