Northwest Chicago Romantic Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Romantic vacation packages in Northwest Chicago

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

Eaglewood Resort and Spa

$415

per person

Nov 2 - Nov 4

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

8.8/10 Excellent! (1,308 reviews)

The Westin Chicago Northwest

$440

per person

Nov 2 - Nov 4

found 20 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

8.8/10 Excellent! (1,024 reviews)

I was surprised by this hotel. A very well-arranged, clean place with welcoming people. I highly recommend it!

Reviewed on Sep 1, 2026

Hyatt Regency Schaumburg Chicago

$532

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip flight included

Albany (ALB) to Chicago (ORD)

8.6/10 Excellent! (1,415 reviews)

Renaissance Schaumburg Convention Center Hotel

$729

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Los Angeles (QLA) to Chicago (ORD)

9/10 Wonderful! (1,016 reviews)

DoubleTree by Hilton Chicago Schaumburg

$466

per person

Oct 6 - Oct 10

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Chicago (ORD)

7.2/10 Good! (1,009 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Northwest Chicago

View all trips

3 Night Romantic vacations in Northwest Chicago

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

The Westin Chicago Northwest

$478

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,024 reviews)

I was surprised by this hotel. A very well-arranged, clean place with welcoming people. I highly recommend it!

Reviewed on Sep 1, 2026

Eaglewood Resort and Spa

$501

per person

Nov 2 - Nov 5

found 1 hour ago

Roundtrip flight included

Pittsburgh (PIT) to Chicago (ORD)

8.8/10 Excellent! (1,308 reviews)

Hyatt Regency Schaumburg Chicago

$556

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

8.6/10 Excellent! (1,415 reviews)

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

$365

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

6.8/10 (1,013 reviews)

Marriott Chicago Schaumburg

$587

per person

Oct 22 - Oct 26

found 19 hours ago

Roundtrip non-stop flight included

Raleigh (RDU) to Chicago (ORD)

8.8/10 Excellent! (1,019 reviews)

Good breakfast

Reviewed on Sep 2, 2026

The Westin Chicago Northwest

$618

per person

Nov 3 - Nov 7

found 22 hours ago

Roundtrip flight included

San Juan (SJU) to Chicago (ORD)

8.8/10 Excellent! (1,024 reviews)

I was surprised by this hotel. A very well-arranged, clean place with welcoming people. I highly recommend it!

Reviewed on Sep 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Chicago

View all trips

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.

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 $365. 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.

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 ...

8.8/10 Excellent! (1,000 reviews)

Couples like: bar, hot tub

Travelers say...

"I was surprised by this hotel. A very well-arranged, clean place with welcoming people. I highly recommend it!"

Reviewed on Sep 1, 2026

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.

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)

"The carpet was clean and not matted down like it so often is in hotels. The room and everything was very clean overall. The bed was super comfortable. Kitchen was well stocked with plates, bowls, silverware, etc. The TVs looked good and the speakers were actually decent. One of the best hotel breakfasts ..."

Reviewed on Aug 24, 2026

See all 3,885 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.