Crestwood Holiday Packages

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Our fantastic packages combine your accommodation and flights to make travelling a breeze.

Exploring Crestwood will be worry free with all those savings.

So, what's stopping you? Act now and save up to . All you need to do is mix and match from more than 550 partner airlines and 665,000 properties.

Some of the most attractive deals available are on Wotif. So zip up your suitcase, dig out your passport and hit the skies!

Crestwood Accommodation

There are just 4 accommodation in Crestwood to pick from. That means your safest bet is to get a wriggle on and secure your room now on Wotif.

Can't get excited about your getaway until you've reserved some accommodation, right? Have a stickybeak at the DoubleTree by Hilton Chicago - Alsip (5000 W 127th St) and the Holiday Inn Express Crestwood (13330 South Cicero Avenue). They're a few of our favourites.

Car Hire in Crestwood

If you're arriving via Midway International Airport, we recommend Budget or Avis. No need to worry about public buses or pricey taxis — these rental outlets are just an easy walk from the baggage claim.

Do you want to hire a set of wheels in the heart of town? Enterprise (12055 S. Cicero) is the closest outlet you'll be able to find. It's just 3 kilometres away.

Holidays to Crestwood

It's time to quit putting all those dreamy travel pics as your wallpaper and make your travel goals come to life in Crestwood. Don't know where to start? With a few basics facts of course.

From the heart of Chicago, you'll need to wander 30 kilometres south to get to Crestwood.

There are loads of amazing people residing in Crestwood, but don't forget to head out and meet some of the folk in the surrounding areas too. Around 2 700 000 people call Chicago home, so you'll definitely make some new pals.

Top Crestwood hotels

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$320 per night from 27 May to 28 May
NZ$320
27 May - 28 May
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
"We had a great stay at this hotel for a long weekend getaway in Chicago (Wed-Sun). The room was generous and quiet. We grabbed lattes at the first-floor bar/ restaurant a few times. The hotel location is awesome, there is a grocery market across the street, easy access to the subway system a few ..."

Reviewed on 9 May 2025

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$319 per night from 26 May to 27 May
NZ$319
26 May - 27 May
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
"I would definitely stay here again. Everything is comfortable and clean. Wish I had more time to explore the area more."

Reviewed on 10 May 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is NZ$229 per night from 26 May to 27 May
NZ$229
26 May - 27 May
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
"No restaurants on site are open."

Reviewed on 12 May 2025

Congress Plaza Hotel
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