Central Chicago Beach Holidays

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Photo by Phil Ostroff

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Top flight + Beach hotel deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
£888
per person
22 Nov - 29 Nov
found 21 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,077
per person
22 Nov - 29 Nov
found 21 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,118
per person
22 Nov - 29 Nov
found 21 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up. Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.

Reviewed on 1 Oct 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,044
per person
22 Nov - 29 Nov
found 21 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,346 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£903
per person
22 Nov - 29 Nov
found 21 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (3,084 reviews)
The room was OK, but the bathroom needed some cleaning. Additionally, only one of the three elevators worked on the morning of our checkout. With the service staff using the one elevator and everyone checking out, it took almost 30 minutes to get from our room to the lobby.

Reviewed on 1 Oct 2026

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5* Beach holidays in Central Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,376
per person
11 Nov - 15 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£1,742
per person
11 Nov - 15 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£1,990
per person
22 Nov - 29 Nov
found 21 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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3 Night Beach holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,770
per person
18 Nov - 21 Nov
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,008
per person
18 Nov - 21 Nov
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£2,397
per person
18 Nov - 21 Nov
found 3 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
See all available trips from London to Central Chicago
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4 Night Beach holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£1,083
per person
11 Nov - 15 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,101
per person
11 Nov - 15 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was, by far, one of the best value-to-cost properties I've stayed with during a work trip. The rooms were clean, the complimentary breakfast was delicious, and the hotel was centrally located. Would definitely stay again!

Reviewed on 1 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,376
per person
11 Nov - 15 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Don't see what you're looking for?
See all available trips from London to Central Chicago
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Find your perfect Central Chicago beach holiday

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

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 Central Chicago 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 Central Chicago?

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 Central Chicago beach holidays, which start from £888. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in Central Chicago?

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

Why should I book family holidays in Central Chicago 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 Central Chicago 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 Central Chicago beach holidays?

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

Can I find Central Chicago beach holidays which are all inclusive?

A beach holiday to Central Chicago 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 Central Chicago 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 Central Chicago beach holiday with Expedia?

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

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Central Chicago

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* 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.