Central Chicago Beach Vacations

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Flight and Beach hotel deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,167
per person
Oct 20 - Oct 23
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,557
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,469
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Clean room

Reviewed on Aug 15, 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
CA $1,491
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Highlights Loved everything about this space! Just look at this breathtaking view. Photos and videos can’t even come close to the real thing. Washer and dryer, fully functional kitchen with nespresso maker, beautiful bathrooms, super comfortable beds, impressively quiet, and the balcony! Perfect location for walking (or short uber ride) to everything. Rooftop pool and hot tub were amazing. Rooms The rooms were massive, beds were so comfortable, and had everything we needed. Location It’s in a perfect location for walking and enjoying the city, without being over crowded. Parking The parking was the only struggled; you have to call and hope someone at the front desk will answer to let you into the garage. It took several calls and walking back into the lobby to get access. Can improve We also didn’t get our free bottle of wine that was promoted on the Expedia listing. There were a lot of spiders on the balcony, but they were harmless web spinners. Amenities The rooftop pool and hot tub added an extra layer of fun to the experience. We didn’t get a chance to experience the arcade, but that was a cool amenity. Noise level Super quiet. The staff Super impressed with the staff, who read my note about this being a special trip, and then giving us a room that exceeding our expectations.

Reviewed on Aug 14, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,160
per person
Oct 19 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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5* Beach holidays in Central Chicago

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

Park Hyatt Chicago

Downtown Chicago
CA $2,408
per person
Oct 19 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $3,362
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,160
per person
Oct 19 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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3 Night Beach holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $1,043
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,266
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,989
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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4 Night Beach holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $1,152
per person
Oct 19 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,655
per person
Oct 19 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,421
per person
Oct 19 - Oct 23
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

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Find the best beach vacations in Central Chicago

What are some benefits when booking beach vacations in Central Chicago?

When you travel to the beach in Central Chicago, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

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

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Central Chicago trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Central Chicago?

There are quite a few things you can do to get cheap beach vacations in Central Chicago. Prices range from CA $1,043, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Central Chicago. These package deals let you save by booking your accommodation and your flight together with savings of up to 26.

Why should I book family beach vacations?

When you're travelling with the family to Central Chicago, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Central Chicago?

It's easy to find a beachfront vacation accommodation in Central Chicago using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Central Chicago as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Central Chicago is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Chicago. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Central Chicago

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
  • 25 min walk from Navy Pier
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very good! (1,995 reviews)
"No microwave or free breakfast in the morning. No coffee or tea maker in the room. The walls are paper thin, so you can hear kids screaming and toilets flushing. The rooms aren’t properly cleaned, as we found a black spider in the bath towels."

Reviewed on Aug 15, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Eurostars Magnificent Mile

Eurostars Magnificent Mile

660 North State Street Chicago IL
  • 17 min walk from Navy Pier
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Eurostars Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL
  • 14 min walk from Navy Pier
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
The Chicago Hotel Collection - Magnificent Mile
See all 1,407 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Central Chicago

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.