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.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was CA $1,126, price is now CA $837 per person
CA $837
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (420 reviews)
Great location off the highway. Short travel distance into downtown Chicago. Great stay!

Reviewed on Jun 19, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.

Reviewed on Jun 16, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,296, price is now CA $921 per person
CA $921
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
We stayed at this hotel for a small wedding venue. I booked the larger room and was glad I did. The hotel was close for walking to restaurants and some bars. The front desk was very friendly and helpful.

Reviewed on Jun 19, 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 $1,424, price is now CA $1,035 per person
CA $1,035
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun

Reviewed on Jun 17, 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
Downtown Chicago

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

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 $192 per night from Jun 30 to Jul 1
CA $192
CA $229 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"The facilities are very old, and there is a musty smell in the room."

Reviewed on Jun 18, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $193 per night from Jun 28 to Jun 29
CA $193
CA $229 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,595 reviews)
"seems like we are visiting every other month to meet up with friends. We have already recommended this hotel many times and will definitely be staying again."

Reviewed on Jun 19, 2026

The Chicago Hotel Collection - Magnificent Mile
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 $191 per night from Jun 28 to Jun 29
CA $191
CA $218 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,669 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."

Reviewed on Jun 17, 2026

Hyatt Regency O'Hare Chicago
See all 4,532 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 $837. 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

8.8/5 (15 reviews)
You can learn about the history of Chicago with a visit to Dearborn Station. Experience the entertainment choices and fascinating museums in this vibrant area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.