Ravenswood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $854, price is now CA $550 per person
CA $550
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Perfect place in the Loop. Customer service was perfect on all fronts.

Reviewed on Sep. 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,841, price is now CA $1,115 per person
CA $1,115
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).

Reviewed on Sep. 8, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,759, price is now CA $1,142 per person
CA $1,142
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Rooms could be updated. Staff was under trained. Amenities very nice, used family room daily with our toddler. Pool deck very modern and new

Reviewed on Sep. 8, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,016, price is now CA $679 per person
CA $679
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on Sep. 4, 2025

Where to stay in Ravenswood

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

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

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 $204 per night from Sep 22 to Sep 23
CA $204
CA $239 total
Sep 22 - Sep 23
includes taxes & fees
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 CA $254 per night from Sep 22 to Sep 23
CA $254
CA $298 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Sep 23 to Sep 24
CA $168
CA $221 total
Sep 23 - Sep 24
includes taxes & fees
Freehand Chicago
See all 4,545 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 $550. 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.

Things to do

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
94% of travellers recommend
Color Factory Chicago Ticket
Spirit of Chicago Lunch Cruise

Spirit of Chicago Signature Lunch Cruise on Lake Michigan

CA $119
per adult
Spirit of Chicago Signature Lunch Cruise on Lake Michigan
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.