Top Beach vacation packages in Central Chicago

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$234

per person

Jan 20 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

Sheraton Grand Chicago Riverwalk

Downtown Chicago

$377

per person

Dec 20 - Dec 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,873 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

$945

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,057 reviews)

The best of the best. The largest rooms in town at the very best price with the very best experience.

Reviewed on Oct 26, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$261

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,105 reviews)

Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$406

per person

Jan 1 - Jan 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (591 reviews)

The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

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5* Beach vacations in Central Chicago

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

The Ritz-Carlton, Chicago

Downtown Chicago

$857

per person

Nov 28 - Dec 1

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,001 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

$945

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,057 reviews)

The best of the best. The largest rooms in town at the very best price with the very best experience.

Reviewed on Oct 26, 2026

Park Hyatt Chicago

Downtown Chicago

$900

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

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3 Night Beach vacations in Central Chicago

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$221

per person

Jan 20 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,334 reviews)

2 adults staying in a room with double beds. Room wasn't that big. Didn't have a closet, buttons on the safe didn't work properly, there was no fridge in the room and there was no cleaning services provided without paying more. It was fine for us as we were only there to sleep, but would be pretty crammed if in a group of 3-4 people. Location was great. Easily accessible by transit and close to the Bean, Boat tour and Art Institute. Overall, found it was a good value considering price point of other comparable hotels, but don't expect any frills while staying.

Reviewed on Oct 26, 2026

Sheraton Grand Chicago Riverwalk

Downtown Chicago

$377

per person

Dec 20 - Dec 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,873 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$234

per person

Jan 20 - Jan 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

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See all available trips from Columbus to Central Chicago

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4 Night Beach vacations in Central Chicago

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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Save 100% on your flight

$278

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,009 reviews)

Sheraton Grand Chicago Riverwalk

Downtown Chicago

$451

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,873 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$319

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

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See all available trips from Columbus to Central Chicago

View all trips

How do I book the best Central Chicago beach vacation packages?

Life’s a beach when you dive into our brilliant Central Chicago beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Central Chicago?

A rental steps from the shore creates an amazingly affordable Central Chicago beach vacation. Seaside sojourns during low season start from $221. Prices and availability are subject to change. Additional terms may apply.

When should I book a Central Chicago beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Central Chicago?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Central Chicago beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Central Chicago vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Central Chicago beach vacation deals?

Sort your search results by deals to delight in amazing Central Chicago beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Central Chicago beach trip with free cancellation and/or flexible dates?

Just like the Central Chicago tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Central Chicago beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Central Chicago. (OK, maybe not that last part.)

Top Beach Central Chicago Hotels

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

9 min drive from McCormick Place

Stroll along the shoreline in Chicago, as you'll be near Oak Street Beach with a holiday at this hotel. Amenities at The Chicago Hotel Collection Ambassador ...

River Hotel

75 East Wacker Drive Chicago IL

6 min drive from McCormick Place

At this hotel, get ready to stroll along the shoreline in Chicago, as you'll be close to the beach. Amenities at River Hotel include a restaurant.

8.8/10 Excellent! (5,575 reviews)

"Not the greatest property, outdated"

Reviewed on Oct 26, 2026

Freehand Chicago

19 East Ohio Street Chicago IL

7 min drive from McCormick Place

Make the most of this fantastic location, as you'll be near the beach with a vacation stay at this hotel. A restaurant, a 24-hour fitness center, and a bar are ...

7.8/10 Good! (3,391 reviews)

"Location was convenient, staff was very helpful. I had a great experience, would stay here again."

Reviewed on Oct 26, 2026

See all 1,398 properties in Central 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.