Printers Row 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 Printers Row

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 $1,271, price is now CA $936 per person
CA $936
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,957 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was CA $1,682, price is now CA $1,151 per person
CA $1,151
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,453, price is now CA $1,031 per person
CA $1,031
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,406, price is now CA $1,017 per person
CA $1,017
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,235, price is now CA $1,619 per person
CA $1,619
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Where to stay in Printers Row

Find the best Printers Row areas and neighborhoods for the activities you enjoy most. Learn more about Printers Row
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

Printers Row 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 $187 per night from Nov 9 to Nov 10
CA $187
CA $223 total
Nov 9 - Nov 10
includes taxes & fees
8/10 Very good! (2,616 reviews)
"I loved the rooftop amenities"

Reviewed on Oct 29, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 24 to Nov 25
CA $162
CA $193 total
Nov 24 - Nov 25
includes taxes & fees
8.8/10 Excellent! (5,570 reviews)
"The rooms need a deep clean, they were clean but stained on the ceiling and carpets. Bed was very worn. Staff were all very nice, from check in to seeing staff in the elevator!"

Reviewed on Oct 29, 2026

River Hotel
See all 4,613 properties in Printers Row
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 Printers Row vacation package cost?
We make it simple to see the world, with Printers Row vacation packages starting from as little as CA $936. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate escape, why not add some tours and activities to your travel itinerary?
How do I get a cheap travel package to Printers Row?
Browse and book everything in the one place with our Printers Row vacation packages. You'll find bargains on hotels, flights, tours and more that'll keep your hip pocket happy and your adventurousness alive. And, with more than 550 air carriers and 1,000,000 properties all over the world to pick from, there are endless opportunities to mix and match as you want.
Where should I stay in Printers Row?
Visitors come from all corners of the globe to see McCormick Place and Millennium Park in Printers Row. Book a hotel within walking distance of these awesome attractions to make sightseeing easy.
How far in advance should I book my Printers Row vacation?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you're booking late, don't fret. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Printers Row travel package include?
From hotels and flights to car rentals, Expedia can help you shape a Printers Row package that suits you. Heading off for a few weeks? Look into a flight, hotel and rental car bundle. If you can only squeeze in a quick getaway, an airfare and hotel deal may be more your style. Tours and activities can be added after you've booked. Our travel packages make it a breeze to plan and save.
What should I know before booking a Printers Row travel package?
A package can be more affordable than separately booking all you need for your adventure. For example, bundle your hotels, flights and rental cars and score impressive savings. Whatever your vacation plans, there's sure to be a package that fits your budget.
Can I choose my airline with a Printers Row Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Simply choose the carrier you want and craft the perfect Printers Row vacation.
If I'm not able to travel, can I cancel my Printers Row vacation package?
Yes, you can. We get that things don't always go to plan, so we're happy to help if you need to make changes to your Printers Row vacation package. It may be possible to change or cancel your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

Stay near popular Printers Row attractions

Dearborn Station

8.8/10 (15 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the fascinating museums and acclaimed art scene in this vibrant area.
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.