
Chicago Romantic Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Romantic hotel deals in Chicago


Trump International Hotel & Tower Chicago
Reviewed on Feb 3, 2026

Pendry Chicago
Reviewed on Jan 31, 2026

Hyatt Centric Chicago Magnificent Mile
Reviewed on Feb 3, 2026

Thompson Chicago, by Hyatt
Reviewed on Jan 14, 2026
5* Romantic holidays in Chicago

Trump International Hotel & Tower Chicago
Reviewed on Feb 3, 2026

Waldorf Astoria Chicago
Reviewed on Jan 26, 2026

Park Hyatt Chicago
Reviewed on Jan 24, 2026
3 Night Romantic holidays in Chicago

Thompson Chicago, by Hyatt
Reviewed on Jan 14, 2026

Pendry Chicago
Reviewed on Jan 31, 2026

Trump International Hotel & Tower Chicago
Reviewed on Feb 3, 2026
4 Night Romantic holidays in Chicago

LondonHouse Chicago, Curio Collection by Hilton
Reviewed on Feb 6, 2026

Waldorf Astoria Chicago
Reviewed on Jan 26, 2026

Trump International Hotel & Tower Chicago
Reviewed on Feb 3, 2026
Plan unforgettable romantic Chicago vacations
What are some of the benefits of booking a romantic Chicago vacation?
When booking a romantic Chicago vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Illinois.
How can I find the best vacation packages for couples?
If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Chicago destination, and you'll be met with an array of options for you and your partner to enjoy.
Can I find cheap romantic vacations for 2 in Chicago?
Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $656 and can enjoy savings of up to 20 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.
What do I need to consider when booking a romantic getaway in Chicago?
Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Chicago certainly come in handy here.
What amenities should I look for in a luxury romantic vacation?
If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Chicago.
Can I book a romantic Chicago vacation with a hot tub?
Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.
How can I find romantic vacation getaways that are all-inclusive?
An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Chicago search.
Can I book a romantic trip to Chicago that is fully refundable?
Several romantic Chicago vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.
Why should I book a romantic vacation with Expedia?
Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.
Romantic Hotels in Chicago

The Champagne Lodge & Luxury Suites
Everything was outstanding
Reviewed on Feb 3, 2026

LondonHouse Chicago, Curio Collection by Hilton
Everything was amazing! View ambience service
Reviewed on Feb 5, 2026

Palmer House a Hilton Hotel
Plenty of lighting in our room. Clean bathroom. Comfortable bed. Nice linens. TV channel choices were good. Lockwood was delicious!
Reviewed on Jan 31, 2026







