
Chicago Romantic Vacations
Best Chicago Romantic packages

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

Eurostars Magnificent Mile
Reviewed on Mar 10, 2025

21c Museum Hotel Chicago
Reviewed on Dec 30, 2024
3 night Chicago Romantic vacation packages with airfare

The Champagne Lodge & Luxury Suites
Reviewed on Jul 11, 2023

21c Museum Hotel Chicago
Reviewed on Dec 30, 2024

Eurostars Magnificent Mile
Reviewed on Mar 10, 2025
4 night Chicago Romantic vacation packages with flight

Ambassador Hotel Chicago
Reviewed on Sep 6, 2024

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

Swissotel - Chicago
Reviewed on Feb 16, 2025
5 night Chicago Romantic vacation packages with airfare included

The Royal Sonesta Chicago River North
Reviewed on Dec 9, 2024

The Godfrey Hotel Chicago
Reviewed on Feb 12, 2025

21c Museum Hotel Chicago
Reviewed on Dec 30, 2024
Romantic vacation packages for 6-7 nights

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

Trump International Hotel & Tower Chicago
Reviewed on Mar 21, 2025

Thompson Chicago, by Hyatt
Reviewed on Feb 9, 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
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- 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