
Irwin Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Better together
Save up to CA $1,096 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 Irwin Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!
Reviewed on Jul. 12, 2025

Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.
Reviewed on Jul. 8, 2025



Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!
Reviewed on Jul. 7, 2025
Irwin Hotel Deals

Comfort Inn Bourbonnais near I-57
1500 Illinois Highway 50, Bourbonnais, IL
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Aug 10 to Aug 11
CA $114
CA $126 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,006 reviews)
Once a year visit to Kankakee
"At check-in there were two ladies at the front desk, very nice and approachable with conversation. I mentioned the convenience of a pool and how my grand-girls were disappointed because the pool wasn't open in July. One of the ladies mentioned that they would cancel my reservations without an issue ..."
Reviewed on Jul. 6, 2025

Best Western Plus Bourbonnais Hotel & Suites
62 Ken Hayes Dr, Bourbonnais, IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jul 16 to Jul 17
CA $118
CA $131 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (446 reviews)
"Overall nice space"
Reviewed on Jul. 9, 2025

Red Roof Inn Bourbonnais
1311 N State Route 50, Bourbonnais, IL
Fully refundableReserve now, pay when you stay
The price is CA $83 per night from Jul 16 to Jul 17
CA $83
CA $92 total
Jul 16 - Jul 17
includes taxes & fees
7.6/10 Good! (230 reviews)
"Very pet friendly!"
Reviewed on Jun. 29, 2025
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
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.