Douglas Holidays from NZ$3,146

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Top Holiday Package Deals in Douglas

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,303, price is now NZ$3,146 per person
NZ$3,146
per person
26 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.

Reviewed on 18 Nov 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was NZ$6,133, price is now NZ$4,038 per person
NZ$4,038
per person
26 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.

Reviewed on 9 Nov 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$5,140, price is now NZ$3,607 per person
NZ$3,607
per person
26 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Perfect stay and location. Room was clean and just what we needed. It’s nothing special

Reviewed on 11 Nov 2025

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Price was NZ$4,753, price is now NZ$3,402 per person
NZ$3,402
per person
26 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.4/10 Exceptional! (983 reviews)
Everything was good

Reviewed on 17 Nov 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,630, price is now NZ$4,802 per person
NZ$4,802
per person
26 Dec - 2 Jan
found 22 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on 17 Nov 2025

Our guide on where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas
Downtown Chicago featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Our pick of the best Douglas Hotel Deals

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$181 per night from 8 Dec to 9 Dec
NZ$181
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (5,271 reviews)
Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt

Reviewed on 18 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$264 per night from 25 Nov to 26 Nov
NZ$264
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (2,057 reviews)
Excellent!

Reviewed on 13 Nov 2025

Palmer House a Hilton Hotel
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$173 per night from 7 Dec to 8 Dec
NZ$173
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,284 reviews)
Amazing

Reviewed on 14 Nov 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,684 properties in Douglas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Douglas holiday package cost?
Tailor make your Douglas holiday package from as little as NZ$3,146. Pick from any combination of hotels, flights and rental cars to craft the escape you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to Douglas?
It's easy. Just bundle. Hotels, rental cars and flights — combine whatever you need into a Douglas holiday package and save. Score even more discounts when you include extras such as experiences or tours to your booking. But that's not the only impressive part. You have the freedom to tailor your trip your way. We offer over 550 airlines and 1 000 000 hotel options globally, so that everyone has an opportunity to travel and live out those holiday dreams.
Where should I stay in Douglas?
Urban explorers come from near and far to experience University of Chicago and Chicago Museum of Science and Industry in Douglas. Book yourself a room close to these popular attractions to make sightseeing easy.
What are the top hotels in Douglas?
Get your trip off to a flying start by booking a stay at Mccormick Place Guest House. It's one of most popular properties in Douglas. Another leading option is Villa Dubois Guest House.
How far in advance should I book my Douglas holiday?
It can be difficult to know exactly when the best time is to book your Douglas holiday. But generally the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels up to a year prior to departure. If you're considering a last-minute getaway, no need to fret! There are terrific deals popping up on Expedia every day.
What does an Expedia Douglas travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to crafting your Douglas trip, you're in control!
What should I know before booking a Douglas travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a neat little package. But hotels aren't your only option. Expedia features all sorts of properties, including holiday homes such as beachside villas and spacious residences. You've got loads of choices!
Can I choose my airline with a Douglas Expedia holiday package?
Yes, you can. We have more than 550 partner airlines all over the world, so choose the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Douglas holiday package?
Yes, you can. We get that things don't always go to plan, so we're here to help if you have to make changes to your Douglas holiday package. You may be able to cancel or change your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Douglas

Supreme Life Building

You can find out about the history of Chicago with a trip to Supreme Life Building. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Supreme Life Building

Activities

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Relax and enjoy the view

Chicago Architecture Center River Cruise aboard First Lady

NZ$97
per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.