Chicago sees New York and raises it deep dish pizzas, the mighty Lake Michigan, and the ex-Playboy Mansion...

5 nights Chicago staying at a 4* hotel with return flights included for £631pp.

Chicago, eh?

Old Hollywood hung out here, the houses are all mansions, and the tree-lined streets are screaming, MONEY HONEY…

Welcome to Chicago’s Gold Coast. The vibes are immaculate.

Days here are spent breaking burrata with mafioso-looking grandads in authentic trattorias and hitting the city beaches. Evenings are for moody cocktail bars, smokey jazz joints, and gallery-hopping.

Where will I sleep?

The kinda lobby that makes us want to light up a fat cigar and burn money…

There’s Mad Men-style wood panelling, amber fireplaces, and low-slung tan sofas in the communal areas, but the cloud-like bedrooms are done in all-white. Oh, and they’ve got 300-thread-count linens and mosaic marble floors… the Patrick Bateman vibes are strong with this one.

Tick off the 24-hour gym and Library bar, but the biggie is the hotel restaurant. Ask for booth 1, it’s where Frank Sinatra used to sit.

What will I do?

Crispy pieces of breaded chicken, ruby-red marinara sauce, and a tangle of spaghetti... Mario’s is a Chicago icon for a reason and it’s literally next door. 3 Arts Club is also just down the street. Go for a garden courtyard restaurant that’s dripping with crystal chandeliers or head down into the wine vault. Bougie but brilliant.

Chicago Old Town has Victorian buildings, comedy clubs, and artisan coffee places. Get your caffeine fix at Kapéj then head to The Second City for your lolz. More of a nature baby? Oak Street Beach and Lincoln Park are both about a 10 minute walk away

Exactly what’s included?

• 5 Nights at the Ambassador Hotel
• Close to beach, restaurants, parks, and galleries
• 24hr gym and iconic restaurant
• Return flights from your choice of airport
• Tap 'Departure Airports' to change
• ATOL protected

Offer in partnership with TUI Holidays, see terms and conditions here.