Ravenswood 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 Ravenswood

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,177, price is now CA $837 per person
CA $837
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Good stay, has the basics for sleeping after a night out. Small but adequate

Reviewed on Oct 31, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,388, price is now CA $1,045 per person
CA $1,045
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,339, price is now CA $1,641 per person
CA $1,641
per person
Jan 17 - Jan 21
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,298, price is now CA $968 per person
CA $968
per person
Jan 21 - Jan 25
found 2 days ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Excellent experience. Thank you.

Reviewed on Oct 31, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,259, price is now CA $941 per person
CA $941
per person
Jan 17 - Jan 21
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Where to stay in Ravenswood

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

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

Ravenswood 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 CA $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
Congress Plaza Hotel
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 $38 per night from Nov 22 to Nov 23
CA $38
CA $242 total
Nov 22 - Nov 23
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundable
The price is CA $166 per night from Nov 23 to Nov 24
CA $166
CA $198 total
Nov 23 - Nov 24
includes taxes & fees
River Hotel
See all 4,746 properties in Ravenswood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Ravenswood vacation package cost?
Get ready to book, because a trip to Ravenswood starts from an affordable CA $837. When you bundle your flights, hotels and more into a travel package, you'll pick up the best bargains.
How do I get a cheap travel package to Ravenswood?
Secure flights that suit your schedule, add a hotel to your booking and watch the savings stack up with a Ravenswood vacation package. It's that simple! From flights and hotels to rental cars and tours, Expedia makes traveling on the cheap easy. And with more than 550 air carriers and 1,000,000 hotel options around the globe to select from, you won't be short of choice.
Where should I stay in Ravenswood?
Stay within a stone's throw of Lincoln Park. This fantastic attraction is in the center of the action and on the must-do lists of most travelers.
What are the top hotels in Ravenswood?
Whether you aim to stay for one night or longer in Ravenswood, you'll get a great night's sleep at The Guesthouse Hotel. This place is popular with many travelers.
How far in advance should I book my Ravenswood vacation?
It all depends on the air carrier, but it's usually possible to look up international fares on Expedia up to 12 months in advance. While it's a good idea to book ahead of time, lucky travelers occasionally nab a cheaper flight just weeks before their intended journey.
What does an Expedia Ravenswood travel package include?
Flights, hotels and a cool set of wheels for your road trip adventures. Simply choose your favorite bundle and get access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings stack up. When it comes to crafting your Ravenswood trip, you're the one in control!
What should I know before booking a Ravenswood travel package?
A travel package can be customized for your circumstances and is a great way to make your money go further. How little or much you include is your call. Hotels, rental cars and flights — come up with a combination that suits your style.
Can I choose my airline with a Ravenswood Expedia vacation package?
You can. We offer more than 550 airline partners worldwide, so fly with the carrier that best fits your travel needs.
If I'm not able to travel, can I cancel my Ravenswood vacation package?
Certainly, and we're here to help. You may be able to cancel or change your Ravenswood vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for more information.

Stay near popular Ravenswood attractions

Black Ensemble Theater

You can make plans for a show at Black Ensemble Theater on your trip to Chicago. Experience the area's theater scene and live music.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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 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.