Douglas Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 4 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Convenient location. The hotel is quiet and staff are helpful and nice.

Reviewed on 14 Nov,2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Dec - 30 Dec
found 4 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
They charge for upgrade.

Reviewed on 14 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 4 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 4 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We thoroughly enjoyed our stay. The staff was courteous and attentive, the room was clean, modern, and comfortable.

Reviewed on 14 Nov,2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 4 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,559 reviews)
excellent staff, great lounge and location

Reviewed on 14 Nov,2024

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

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Douglas

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 S$137 per night from 24 Nov to 25 Nov
S$137
includes taxes & fees
24 Nov - 25 Nov
7.8/10 Good! (8,066 reviews)
"Every staff member we met greeted us with a smile and were at the ready to answer any questions we had. My son and I were so excited to stay here and we will definitely be back."

Reviewed on 13 Nov,2024

Congress Plaza Hotel
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 S$187 per night from 8 Dec to 9 Dec
S$187
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,184 reviews)
"Our family loved the breakfast buffet, reception every evening, and the pool."

Reviewed on 12 Nov,2024

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 16 Dec to 17 Dec
S$153
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (3,530 reviews)
"Nice"

Reviewed on 12 Nov,2024

River Hotel
See all 4,062 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 S$707. 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 rentals 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.

Things to do

Dock and Dine along the river!

Private Chicago 6-Hour Boat Tour with Captain

S$2,857
Per adult
Private Chicago 6-Hour Boat Tour with Captain
Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

S$58
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.