![](https://forever.travel-assets.com/flex/flexmanager/images/2020/06/26/Orbitz-wizard-background.jpg?impolicy=fcrop&w=900&h=225&q=mediumHigh)
Chicago Romantic Vacations
Best Chicago Romantic packages
![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Virgin Hotels Chicago
Reviewed on May 12, 2024
![W Chicago - City Center](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/ad18e96a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
W Chicago - City Center
Reviewed on Feb 18, 2024
![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/425695dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Trump International Hotel & Tower Chicago
Reviewed on Apr 2, 2024
3 night Chicago Romantic vacation packages with airfare
![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Virgin Hotels Chicago
Reviewed on May 12, 2024
![W Chicago - City Center](https://images.trvl-media.com/lodging/1000000/30000/23500/23481/ad18e96a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
W Chicago - City Center
Reviewed on Feb 18, 2024
![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/425695dc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Trump International Hotel & Tower Chicago
Reviewed on Apr 2, 2024
4 night Chicago Romantic vacation packages with flight
![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/ac62e1c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Palmer House a Hilton Hotel
Reviewed on Mar 25, 2024
![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Virgin Hotels Chicago
Reviewed on May 12, 2024
![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/2a95e836_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Allegro Royal Sonesta Hotel Chicago Loop
Reviewed on Apr 12, 2024
Romantic vacation packages for 6-7 nights
![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Virgin Hotels Chicago
Reviewed on May 12, 2024
![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
LondonHouse Chicago, Curio Collection by Hilton
Reviewed on Mar 31, 2024
![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/f201150c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Pendry Chicago
Reviewed on Apr 5, 2024
Romantic hotels in Chicago
![The Champagne Lodge & Luxury Suites](https://images.trvl-media.com/lodging/2000000/1800000/1791800/1791716/828d8e06_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Champagne Lodge & Luxury Suites
![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
LondonHouse Chicago, Curio Collection by Hilton
![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/ac62e1c3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
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.