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*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

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Top Holiday Package Deals in Printers Row

Price found within the past 48 hours. Click for updated prices.
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

Downtown Chicago
CA $686
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,004 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,311
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
CA $886
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
We had a lovely stay. The coffee downstairs is excellent!

Reviewed on Sep 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,121
per person
Oct 15 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
CA $788
per person
Oct 22 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,334 reviews)
Hidden fees

Reviewed on Sep 11, 2026

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.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Printers Row Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $176
CA $210 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (5,432 reviews)
"."

Reviewed on Sep 12, 2026

River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $248
CA $295 total
Oct 13 - Oct 14
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $220
CA $262 total
Sep 27 - Sep 28
includes taxes & fees
Congress Plaza Hotel
See all 4,450 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.

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 $686. 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 $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
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.