West Side Beach Holidays

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Top flight + Beach hotel deals in West Side

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
£1,136
per person
19 Oct - 26 Oct
found 9 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,509
per person
19 Oct - 26 Oct
found 9 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on 17 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,348
per person
19 Oct - 26 Oct
found 9 hours ago
Return direct flight included
Edinburgh (EDI) 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 12 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,978
per person
19 Oct - 26 Oct
found 9 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
£1,441
per person
19 Oct - 26 Oct
found 9 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
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5* Beach holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,978
per person
19 Oct - 26 Oct
found 9 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 Aug 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£2,324
per person
26 Sept - 2 Oct
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,695
per person
26 Sept - 2 Oct
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Edinburgh to West Side
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3 Night Beach holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

Downtown Evanston
£1,028
per person
21 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (99 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£1,792
per person
21 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.

Reviewed on 16 Aug 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare
£1,066
per person
21 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very good! (2,362 reviews)
Don't see what you're looking for?
See all available trips from London to West Side
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4 Night Beach holidays in West Side

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

Swissotel - Chicago

Downtown Chicago
£1,250
per person
22 Oct - 26 Oct
found 1 hour ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.

Reviewed on 17 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,297
per person
22 Oct - 26 Oct
found 1 hour ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on 17 Aug 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£1,525
per person
8 Oct - 12 Oct
found 14 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Don't see what you're looking for?
See all available trips from London to West Side
View all trips

Find your perfect West Side beach holiday

How can I book the best beach holidays in West Side?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your West Side beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in West Side?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable West Side beach holidays, which start from £1,028. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in West Side?

Enjoy out-of-season seclusion on a beach holiday to West Side during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in West Side with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a West Side beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute West Side beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in West Side. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find West Side beach holidays which are all inclusive?

A beach holiday to West Side is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a West Side beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a West Side beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in West Side on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in West Side

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Where to go when
Where to go when

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.