Douglas Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Downtown Chicago

5 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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$271 per night from 25 May to 26 May
NZ$271
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"As one of my first solo trips, I was glad to feel very safe and comfortable during my stay. I had requested and paid extra for a lake front room. On the fourth floor I could barely see the lake, but did face the park. Good news and bad news because the street noise was very loud at times. I ate in ..."

Reviewed on 22 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$372 per night from 27 May to 28 May
NZ$372
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,211 reviews)
"I do a lot of traveling was very impressed by the staff money well spend"

Reviewed on 23 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$247 per night from 25 May to 26 May
NZ$247
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,455 reviews)
"the rooftop was great, room was clean, overall good for the price"

Reviewed on 22 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,671 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 . 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 art galleries in this vibrant area.

Supreme Life Building

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.