Northwest Side Beach Holidays

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  • Rest easy

    Packages with flights are ATOL protected

Top flight + Beach hotel deals in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
£826
per person
25 Nov - 28 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,313
per person
26 Nov - 30 Nov
found 24 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
£1,382
per person
30 Dec - 4 Jan
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,525
per person
30 Dec - 4 Jan
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,213
per person
5 Dec - 12 Dec
just found
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
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5* Beach holidays in Northwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,313
per person
26 Nov - 30 Nov
found 24 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,525
per person
30 Dec - 4 Jan
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£1,508
per person
31 Dec - 4 Jan
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (939 reviews)
Don't see what you're looking for?
See all available trips from London to Northwest Side
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3 Night Beach holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
£826
per person
25 Nov - 28 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
£861
per person
25 Nov - 28 Nov
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,051
per person
13 Jan - 16 Jan
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Don't see what you're looking for?
See all available trips from London to Northwest Side
View all trips

4 Night Beach holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

Downtown Chicago
£755
per person
25 Dec - 29 Dec
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,313
per person
26 Nov - 30 Nov
found 24 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£990
per person
26 Nov - 30 Nov
found 24 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Don't see what you're looking for?
See all available trips from London to Northwest Side
View all trips

Find your perfect Northwest Side beach holiday

How can I book the best beach holidays in Northwest 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 Northwest 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 Northwest 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 Northwest Side beach holidays, which start from £755. Prices and availability are subject to change. Additional terms may apply.

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

Enjoy out-of-season seclusion on a beach holiday to Northwest 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 Northwest 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 Northwest 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 Northwest Side beach holidays?

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

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

A beach holiday to Northwest 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 Northwest 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 Northwest Side beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in Northwest 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

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Northwest Side

More holidays you might like

* 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.