Romantic Vacations in Northwest Side 2026

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4 Night Romantic holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,282

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

not enough to do no more eating hours

Reviewed on Aug 16, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,603

per person

Oct 11 - Oct 15

just found

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $2,177

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,638 reviews)

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What are some of the benefits of booking a romantic Northwest Side vacation?

When booking a romantic Northwest Side 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 Chicago.

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 Northwest Side 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 Northwest Side?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $1,282 and can enjoy savings of up to 33 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 Northwest Side?

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 Northwest Side 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 Northwest Side.

Can I book a romantic Northwest Side 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 Northwest Side search.

Can I book a romantic trip to Northwest Side that is fully refundable?

Several romantic Northwest Side 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.