Northwest Chicago Romantic Vacations 2026

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Top Romantic vacation packages in Northwest Chicago

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

The Westin Chicago Northwest

$319

per person

Dec 18 - Dec 20

found 15 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,013 reviews)

Eaglewood Resort and Spa

$559

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip flight included

Miami (MIA) to Chicago (ORD)

8.8/10 Excellent! (1,367 reviews)

Renaissance Schaumburg Convention Center Hotel

$686

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Chicago (ORD)

9/10 Wonderful! (1,002 reviews)

Hyatt Regency Schaumburg Chicago

$420

per person

Dec 18 - Dec 20

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

8.6/10 Excellent! (1,484 reviews)

Good breakfast buffet, safe and plenty parking

Reviewed on Oct 17, 2026

DoubleTree by Hilton Chicago Schaumburg

$574

per person

Nov 29 - Dec 1

found 23 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Chicago (ORD)

7.2/10 Good! (1,004 reviews)

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See all available trips from Columbus to Northwest Chicago

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3 Night Romantic vacations in Northwest Chicago

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

Eaglewood Resort and Spa

$317

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,367 reviews)

The Westin Chicago Northwest

$350

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,013 reviews)

Hyatt Regency Schaumburg Chicago

$363

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,484 reviews)

Good breakfast buffet, safe and plenty parking

Reviewed on Oct 17, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Chicago

View all trips

4 Night Romantic vacations in Northwest Chicago

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

Wyndham Garden Schaumburg Chicago Northwest

$490

per person

Dec 18 - Dec 22

found 4 hours ago

Roundtrip flight included

Greensboro (GSO) to Chicago (ORD)

6.8/10 (1,006 reviews)

Eaglewood Resort and Spa

$549

per person

Dec 18 - Dec 22

found 4 hours ago

Roundtrip flight included

Greensboro (GSO) to Chicago (ORD)

8.8/10 Excellent! (1,367 reviews)

Country Inn & Suites by Radisson, Schaumburg, IL

$500

per person

Dec 18 - Dec 22

found 4 hours ago

Roundtrip flight included

Greensboro (GSO) to Chicago (ORD)

8.8/10 Excellent! (1,394 reviews)

Staff was great

Reviewed on Oct 15, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Chicago

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How can I find the best Northwest Chicago vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Northwest Chicago romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of .

How can I plan a great romantic trip to Northwest Chicago?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Northwest Chicago?

Put a price on love with stunning deals for duos starting at just $317. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply.

Can I book Northwest Chicago spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

What’s the best time of year for a romantic vacation in Northwest Chicago?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

How can I book romantic weekend getaway packages in Northwest Chicago?

To book a loved-up break in Northwest Chicago, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Northwest Chicago with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Northwest Chicago romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Northwest Chicago Hotels

The Westin Chicago Northwest

400 Park Blvd Itasca IL

10 min drive from Woodfield Mall

Rekindle the romance with your special someone. Consider booking a getaway at this hotel where you're sure to love the hot tub and garden. Other amenities to ...

Embassy Suites by Hilton Chicago Schaumburg Woodfield

1939 N Meacham Rd Schaumburg IL

27 min walk from Woodfield Mall

Enjoy a stay at this romantic hotel, featuring onsite dining and a bar for couples to enjoy.

8.6/10 Excellent! (1,005 reviews)

"Some elevator issues"

Reviewed on Oct 17, 2026

Homewood Suites by Hilton Chicago - Schaumburg

815 East American Lane Schaumburg IL

11 min walk from Woodfield Mall

If you're looking for a special getaway, consider a stay at this romantic hotel where there's a terrace and much more for you and your partner to enjoy.

8.8/10 Excellent! (1,000 reviews)

"Nice"

Reviewed on Oct 12, 2026

See all 4,015 properties in Northwest Chicago

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.