Chicago Beach Holidays

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Chicago beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Chicago beach holidays, which start from £539. Prices and availability are subject to change. Additional terms may apply.

Enjoy out-of-season seclusion on a beach holiday to Chicago during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

Add a little spontaneity to your beach holiday by looking for a last-minute deal in Chicago. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

A beach holiday to Chicago is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Our huge range of accommodation and flights mean you’ll find the best beach holidays in Chicago on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.