Top Beach vacation packages in Chicago

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

Renaissance Chicago North Shore Hotel

$392

per person

Jul 12 - Jul 15

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Chicago (ORD)

8.4/10 Very Good! (1,005 reviews)

I love everything about Renaissance Chicago north shore hotel, they made my trip in Chicago a memorable one. I will recommend it to anyone

Reviewed on May 7, 2026

Eurostars Magnificent Mile

Downtown Chicago

$442

per person

Jun 11 - Jun 13

found 14 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,506 reviews)

The panoramic room is the best because the views at night

Reviewed on May 11, 2026

The Wheeler Mansion

Near South Side

$1,116

per person

Jul 16 - Jul 19

found 12 hours ago

Roundtrip flight included

Philadelphia (PHL) to Chicago (ORD)

9/10 Wonderful! (4 reviews)

A unique place to stay near the convention centre.

Reviewed on Jun 23, 2025

Graduate by Hilton Evanston

Downtown Evanston

$841

per person

Jun 16 - Jun 19

found 1 day ago

Roundtrip flight included

Wilmington (ILM) to Chicago (ORD)

9/10 Wonderful! (1,004 reviews)

The Graduate is very charming and I had a special room with a view and a fireplace! But it comes with all the charm of a boutique hotel, like a slow elevator (and only one small elevator), so don't expect the perks and efficiency of a franchise hotel. But I still prefer it and it feels more like home. I'll stay there again when I'm in Evanston!

Reviewed on May 6, 2026

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

$802

per person

Jul 15 - Jul 18

found 23 hours ago

Roundtrip flight included

Wichita (ICT) to Chicago (ORD)

8.8/10 Excellent! (2,451 reviews)

The staff was extremely polite, and the hotel was in the most convenient area for the activities we were doing. Great visit!

Reviewed on May 11, 2026

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5* Beach vacations in Chicago

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

Four Seasons Hotel Chicago

Downtown Chicago

$1,245

per person

Jul 12 - Jul 15

found 18 hours ago

Roundtrip flight included

Albuquerque (ABQ) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Loved our suite- gorgeous views! Great service and excellent location

Reviewed on May 8, 2026

The Ritz-Carlton, Chicago

Downtown Chicago

$2,981

per person

Jun 11 - Jun 14

found 11 hours ago

Roundtrip flight included

Memphis (MEM) to Chicago (ORD)

9.2/10 Wonderful! (1,001 reviews)

Excellent experience

Reviewed on May 11, 2026

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3 Night Beach vacations in Chicago

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

Eurostars Magnificent Mile

Downtown Chicago

$770

per person

Jun 11 - Jun 14

found 10 hours ago

Roundtrip flight included

Allentown (ABE) to Chicago (ORD)

9/10 Wonderful! (3,506 reviews)

The panoramic room is the best because the views at night

Reviewed on May 11, 2026

Thompson Chicago, by Hyatt

Downtown Chicago

Save 100% on your flight

$932

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,361 reviews)

This is our favorite hotel in chicago. Great location and staff. Rooms very comfortable.

Reviewed on May 11, 2026

Swissotel - Chicago

Downtown Chicago

$1,150

per person

Jul 12 - Jul 15

found 18 hours ago

Roundtrip flight included

Albuquerque (ABQ) to Chicago (ORD)

9/10 Wonderful! (3,303 reviews)

we didn't have breakfast at the hotel

Reviewed on May 11, 2026

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4 Night Beach vacations in Chicago

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

Thompson Chicago, by Hyatt

Downtown Chicago

$746

per person

Jul 13 - Jul 17

found 18 hours ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

9.2/10 Wonderful! (1,361 reviews)

This is our favorite hotel in chicago. Great location and staff. Rooms very comfortable.

Reviewed on May 11, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$1,024

per person

Jun 11 - Jun 15

found 1 day ago

Roundtrip non-stop flight included

Amarillo (AMA) to Chicago (ORD)

9/10 Wonderful! (3,303 reviews)

we didn't have breakfast at the hotel

Reviewed on May 11, 2026

Eurostars Magnificent Mile

Downtown Chicago

$1,021

per person

Jun 11 - Jun 15

found 1 day ago

Roundtrip non-stop flight included

Amarillo (AMA) to Chicago (ORD)

9/10 Wonderful! (3,506 reviews)

The panoramic room is the best because the views at night

Reviewed on May 11, 2026

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How do I book the best Chicago beach vacation packages?

Life’s a beach when you dive into our brilliant 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 Chicago?

A rental steps from the shore creates an amazingly affordable Chicago beach vacation. Seaside sojourns during low season start from $392. Prices and availability are subject to change. Additional terms may apply.

When should I book a 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 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 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 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 Chicago beach vacation deals?

Sort your search results by deals to delight in amazing 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 Chicago beach trip with free cancellation and/or flexible dates?

Just like the 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 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 Chicago. (OK, maybe not that last part.)

Top Beach Chicago Hotels

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

9 min drive from Wrigley Field

Recharge at this hotel and enjoy the sunsets on the beach in Chicago, as you'll be near Oak Street Beach. Amenities at Hilton Chicago/Magnificent Mile Suites ...

9/10 Wonderful! (4,301 reviews)

Travelers like: close to beach, indoor pool

Travelers say...

Very nice hotel in a great location.

Reviewed on May 12, 2026

River Hotel

75 East Wacker Drive Chicago IL

11 min drive from Wrigley Field

Settle in and relax at this hotel and get ready to stroll along the shoreline in Chicago, as you'll be near Ohio Street Beach. Amenities at River Hotel include ...

8.8/10 Excellent! (5,198 reviews)

Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!

Reviewed on May 11, 2026

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St Chicago IL

10 min drive from Wrigley Field

Relax at this hotel and lounge by the shoreline in Chicago, as you'll be near Oak Street Beach. Amenities at DoubleTree by Hilton Chicago - Magnificent Mile ...

8.8/10 Excellent! (2,476 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

The warm cookies at check in were the absolute best!!

Reviewed on May 11, 2026

See all 5,548 properties in 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.