Top Beach vacation packages in Central Chicago

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$270

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (3,148 reviews)

The bathroom in my room was looking worse for wear, broken tiles and caulk missing. However the room itself was clean and staff was sooooo helpful and courteous which made my stay great! I even was out of body wash and the girl at the front desk made sure I got some after house keeping didn’t bring any after an hour and I wanted to shower. Good people working here!

Reviewed on Oct 28, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$437

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

Great location, nice rooms, nice rooftop bar and large breakfast buffet included.

Reviewed on Oct 28, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$379

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$294

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,334 reviews)

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$391

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,572 reviews)

Hotel smells amazing

Reviewed on Oct 28, 2026

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5* Beach vacations in Central Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago

$776

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,057 reviews)

The Peninsula Chicago

Downtown Chicago

$828

per person

Jan 8 - Jan 11

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Downtown Chicago

$1,406

per person

Dec 23 - Dec 28

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 Riu Plaza Chicago

Downtown Chicago

$300

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,555 reviews)

Great location, nice rooms, nice rooftop bar and large breakfast buffet included.

Reviewed on Oct 28, 2026

Sheraton Grand Chicago Riverwalk

Downtown Chicago

$410

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)

My experience at the Sheraton was terrible. I was assigned a room right next to the elevator, where there was also a shared microwave for guests on the floor. A large group of young people was placed in the same hallway. They appeared to be intoxicated and made excessive noise from around 11 p.m. until nearly 4 a.m., making it impossible to sleep. I called the front desk three times asking for help, but the noise continued and nothing was resolved. I felt very unsafe and completely let down by the hotel staff. Guests should be able to expect a restful stay and a response when they ask for help. I left exhausted and deeply disappointed. I expected much better from the Sheraton.

Reviewed on Oct 28, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$379

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

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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

$288

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)

The staff is very friendly and professional.

Reviewed on Oct 27, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$329

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)

Great location, nice rooms, nice rooftop bar and large breakfast buffet included.

Reviewed on Oct 28, 2026

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$294

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (2,334 reviews)

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See all available trips from Columbus to Central Chicago

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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 $270. 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! (5,568 reviews)

"Cool old building with a beautiful lobby (retro). Room was skinny, but so is the building. AC was loud in room, but worked well. Bed was ok, but had a big dip in it on one side. Room was very clean and housekeeping cleaned each day, unlike many hotels that do not. View was nice of river, but window ..."

Reviewed on Oct 28, 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! (3,396 reviews)

"Avoid this hotel. The lobby and room was dirty, there was no soap or shampoo in the bathroom, the room next to me was kicked in by police arresting someone. Hideous experience."

Reviewed on Oct 28, 2026

See all 1,396 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.