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Northwest Chicago Romantic Vacations

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Top Romantic vacation packages in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
  • Sept 4 - Sept 6

    Holiday Inn Express & Suites Chicago West-Roselle by IHG + Flight

    Roselle
    2 nights
    2.5 star property
    7.8/10 - Good (1,004 reviews)
    Roundtrip Toronto (YYZ) - Chicago (ORD)
    YYZ - ORDNonstop ORD - YYZNonstop
    CA $570
    CA $559
    per traveller
    found 1 day ago
    Holiday Inn Express & Suites Chicago West-Roselle by IHG
  • Sept 5 - Sept 8

    Eaglewood Resort and Spa + Flight

    Itasca
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,221 reviews)
    Roundtrip Hamilton (YHM) - Chicago (ORD)
    YYZ - ORDNonstop ORD - YTZNonstop
    CA $883
    CA $762
    per traveller
    found 16 hours ago
    Eaglewood Resort and Spa
  • Oct 8 - Oct 12

    The Westin Chicago Northwest + Flight

    Itasca
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,003 reviews)
    Roundtrip Montreal (YMQ) - Chicago (ORD)
    YUL - ORD1 stop ORD - YUL1 stop
    CA $1,170
    CA $1,084
    per traveller
    found 1 day ago
    The Westin Chicago Northwest
  • Sept 4 - Sept 6

    Hyatt Regency Schaumburg Chicago + Flight

    Schaumburg
    2 nights
    4.0 star property
    8.6/10 - Excellent (1,368 reviews)
    "I’ve stayed at this hotel at least 50 times. Always has been my “go to”. Sadly, the experience was less than my usual expectation. It was Friday night 4:15 pm, went to check in and work a few more hours. They had no linens. Finally, 6:30 pm I got to the room. Air conditioning was not working properly, Hot! Room, and hallway smelled of mildew. Carpet was old and sagging. Coffee pot not working. 1 towel, 1 washcloth, no hand towels, no bath mat. This room was over $200 for less than 12 hours...."
    Reviewed July 19, 2026
    Roundtrip Montreal (YMQ) - Chicago (ORD)
    YUL - ORDNonstop ORD - YULNonstop
    CA $739
    CA $704
    per traveller
    found 1 day ago
    Hyatt Regency Schaumburg Chicago
  • Aug 22 - Aug 25

    Renaissance Schaumburg Convention Center Hotel + Flight

    Schaumburg
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Great!"
    Reviewed July 16, 2026
    Roundtrip Toronto (YTO) - Chicago (ORD)
    YTZ - MDWNonstop MDW - YTZNonstop
    CA $866
    CA $845
    per traveller
    found 9 hours ago
    Renaissance Schaumburg Convention Center Hotel

Discover the most popular places to visit in Northwest Chicago

What to do in Northwest Chicago

Top Romantic Northwest Chicago Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Plan unforgettable romantic Northwest Chicago vacations

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

When booking a romantic Northwest 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 Northwest 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 Northwest 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 $559 and can enjoy savings of up to 1 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 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 Northwest 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 Northwest Chicago.

Can I book a romantic Northwest 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 Northwest Chicago search.

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

Several romantic Northwest 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.