Chicago Romantic Holidays

Find your dream romantic Chicago getaway on Expedia. From secluded hideaways to blissful spa treatments and charming country escapes, we’ve got it all. Just activate our “romantic” filters to uncover your ideal couple’s retreat in Chicago.

Unveil the perfect and budget-friendly romantic getaways in Chicago with Expedia. Our filters unlock countless options, ensuring a heart-pounding experience. Set budget filters to match your spending limits and sort by price to prioritise the most affordable options in your search results.

In your search, you can apply search filters for Chicago trip packages and sort your results to see the romantic getaway options first. With those standards, you could find amazing romantic holiday options in Chicago, from winter getaways to secluded country or budget beach holidays with your loved one.

Plan your ultimate couple’s getaway in Chicago with our user-friendly search tools. Opt for a hotel suite with a view worth sharing on Instagram. Cruise with the top down and feel the warm breeze in your hair with a luxury car hire. Decide on a romantic couple’s spa treatment, a beachfront candle-lit dinner, or a glamorous night out on the town.

For last-minute romantic holiday package deals in Chicago, enter your travel dates into the search and discover available deals. Customise your search with filters, covering amenities, price, star rating, and more to find your ideal romantic package for couples.

Refine your search with the “pet-friendly” filter to discover top pet-welcoming hotels and resorts in Chicago. Experience a couple’s treatment, bask in beautiful surroundings, and revel in a pampering romantic getaway, knowing your pet is either by your side or well cared for in doggy day care.

Escape the weekly grind with fantastic couple’s weekend getaways in Chicago. Enter your location and date preferences in your Expedia search and let us reveal hidden gems to leave you refreshed and love-struck for the week ahead.

Discover the ultimate luxury romantic packages in Chicago with ease. Use the site’s or app’s search function to explore a range of lavish options, as well as to refine your choices by star rating and price.

Choose from our latest incredible deals or customise your trip in just a few clicks, with simple search and filter functions that make finding your next romantic Chicago getaway easy. Plus, booking a package with Expedia could save you money, too, making a Chicago holiday for couples all the more attractive.