Douglas Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Holiday Package Deals in Douglas

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $876, price is now CA $641 per person
CA $641
per person
Sep 23 - Sep 25
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I enjoyed my stay here. Clean room, well maintained property and great location just 3 miles from Chicago. The best part was the friendly staff. The breakfast was a 4.5 out 5, just adequate foe the day's need, nothing super special. I would definitely return.

Reviewed on Jul 13, 2026

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Price was CA $1,073, price is now CA $732 per person
CA $732
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
Great stay perfect location

Reviewed on Jul 12, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,871, price is now CA $1,286 per person
CA $1,286
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that looked a little tired and could use updating but overall we had a good sleep and were refreshed for the next day.

Reviewed on Jul 13, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,089, price is now CA $1,466 per person
CA $1,466
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
It has a good view but for the price we pay it should offer more.

Reviewed on Jul 14, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,443, price is now CA $1,047 per person
CA $1,047
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Clean rooms, nice pool, location great

Reviewed on Jul 12, 2026

Where to stay in Douglas

Find the best Douglas areas and neighborhoods for the activities you enjoy most. Learn more about Douglas
A busy city street with tall buildings, a bus, and cars.

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

Douglas Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 3 to Aug 4
CA $239
CA $273 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,839 reviews)
"Clean rooms nice hotel"

Reviewed on Jul 14, 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Jul 27 to Jul 28
CA $230
CA $274 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,745 reviews)
"The property is located near the beach and restaurants. It’s ideal for accessibility. Unfortunately our hotel room shower was broken. The bathroom was in poor condition and had not been maintained."

Reviewed on Jul 13, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $333 per night from Jul 26 to Jul 27
CA $333
CA $443 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,917 reviews)
"While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that ..."

Reviewed on Jul 13, 2026

Omni Chicago Hotel
See all 4,445 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.
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Frequently asked questions

How much does a Douglas vacation package cost?
Tailor make your Douglas vacation package from as little as CA $641. 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 vacation 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 vacation 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 vacation?
It can be difficult to know exactly when the best time is to book your Douglas vacation. 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 vacation rentals such as beachside villas and spacious residences. You've got loads of choices!
Can I choose my airline with a Douglas Expedia vacation 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 vacation 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 vacation 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.

Stay near popular Douglas attractions

Illinois Institute of Technology

7.0/10 (4 reviews)
Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $71
per adult
94% of travellers recommend
Chicago By Night 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.