Central Chicago Beach Holidays 2026

Photo by Phil Ostroff

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Top flight + Beach hotel deals in Central Chicago

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

AU$1,156

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on 8 Dec 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

AU$2,044

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.

Reviewed on 11 Dec 2025

Hotel Riu Plaza Chicago

Downtown Chicago

AU$1,185

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Love the staff here. Great stay all the way around! I was in 2409. Quiet room.

Reviewed on 11 Dec 2025

Pendry Chicago

Downtown Chicago

AU$1,319

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on 4 Dec 2025

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

AU$1,774

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

8.2/10 Very Good! (2,158 reviews)

It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.

Reviewed on 6 Dec 2025

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5* Beach holidays in Central Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

AU$2,044

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.

Reviewed on 11 Dec 2025

Nobu Hotel Chicago

Downtown Chicago

AU$2,919

per person

12 Jan - 19 Jan

found 1 day ago

Return direct flight included

Mexico City (MEX) to Chicago (ORD)

9.4/10 Exceptional! (748 reviews)

the room was an old remolded warehouse and the concrete ceiling was not painted, however that did not distract from the area ( safe) and quality of amenities. I had room service every day, and that was $$$ if was a little disappointing ( the breakfast eggs cold when they arrived) it was a fun and fantastic stay.

Reviewed on 9 Dec 2025

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See all available trips from Columbus to Central Chicago

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How can I book a Central Chicago beach holiday package with Expedia?

Beach holidays to beach holidays on Expedia?

To find your ideal family-friendly Central Chicago beach holiday package, simply use the site’s or the app’s search function to explore diverse packages tailored to your chosen destination. Refine your search with filters to narrow down options based on your favourite amenities.

How can I select the perfect beach holiday package for Central Chicago?

Customise your quest for Central Chicago beach holiday packages, including flights, with search filters and prioritise your preferred options. This way, you’ll uncover fantastic beach holidays, whether it’s a romantic beach escape, a luxurious beach package, or a surfers’ paradise in Central Chicago.

How can I find the best Central Chicago beach holiday deals?

Grab some of the best Central Chicago beach holiday deals by being flexible with your destination and dates, ideally travelling outside of peak seasons. If you have specific seas in mind, enter the details and apply filters to uncover a budget-friendly trip.

How can I discover last-minute Central Chicago beach holiday deals?

If you love a last-minute deal, you’ve come to the right place. Select our top picks or customise your beach getaway in Central Chicago using date and destination filters. Bundle accommodation, airfare, and car rental for the best value. Tailor your search with filters covering amenities, price, star rating, and more.

How can I find pet-friendly Central Chicago beach holiday packages?

Indulge yourself and your furry companion in Central Chicago’s pet-friendly beach holiday options. Enhance your getaway with our filters, including doggy day care, divine pet-friendly beach apartments, and access to pet-friendly local beaches.

When are the best times to go for a Central Chicago beach holiday?

For the ultimate Central Chicago beach holiday, choose summer for vibrant energy. Alternatively, opt for winter to enjoy a tranquil, less crowded experience with ample alone time.