
Northwest Side Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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
Top Romantic vacation packages in Northwest Side

Pendry Chicago
Reviewed on Dec 4, 2025

Level Chicago – Old Town
Reviewed on Dec 9, 2025

Trump International Hotel & Tower Chicago
Reviewed on Dec 8, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Dec 9, 2025

La Banque Hotel
Reviewed on Nov 30, 2025
5* Romantic vacations in Northwest Side

Trump International Hotel & Tower Chicago
Reviewed on Dec 8, 2025

The Langham, Chicago
Reviewed on Dec 1, 2025

Four Seasons Hotel Chicago
Reviewed on Nov 26, 2025
3 Night Romantic vacations in Northwest Side

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Dec 9, 2025

La Banque Hotel
Reviewed on Nov 30, 2025

Virgin Hotels Chicago
Reviewed on Nov 26, 2025
4 Night Romantic vacations in Northwest Side

The Emily Hotel
Reviewed on Nov 26, 2025

Trump International Hotel & Tower Chicago
Reviewed on Dec 8, 2025

Level Chicago – Old Town
Reviewed on Dec 9, 2025
How to find a romantic Northwest Side vacation
How can I find the best Northwest Side 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 Side 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 Side?
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 Side?
Put a price on love with stunning deals for duos starting at just $254. 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 Side 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 Side?
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 Side?
To book a loved-up break in Northwest Side, 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 Side 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 Side 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?



















