Irwin Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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Top Irwin vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 7 - Jan 11

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,566 reviews)
    "Breakfast was good"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,051
    CA $758
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $2,739
    CA $1,191
    per traveller
    found 23 hours ago
    Sheraton Grand Chicago Riverwalk
  • Dec 27 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    Save 100% on your flight
    CA $3,612
    CA $2,536
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • Jan 7 - Jan 11

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,357 reviews)
    "Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,190
    CA $853
    per traveller
    found 1 day ago
    The Emily Hotel
  • Jan 7 - Jan 11

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,044
    CA $760
    per traveller
    found 1 day ago
    Level Chicago Fulton Market

Irwin Hotel Deals

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 an Irwin vacation package cost?

Offering excellent value package deals from CA $758 on Expedia, you'll be surprised at how little a vacation to Irwin costs! Expedia's packages make travel planning easier and your savings go further.

What are the cheapest months to go to Irwin?

January, February and November are great times to look for cheap Irwin vacation packages. Opting to travel in quieter months means you can generally find reduced prices on hotels and flights.

How many days is enough for Irwin?

Generally, a handful of days is enough to tick off the top attractions during your Irwin vacation. However, if you prefer to have time to kick back or go on day tours, consider extending your trip.

How to find the best Irwin package deals?

Begin your search for an Irwin package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Irwin package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Irwin adventure off to a flying start.

Is it cheaper to book an Irwin vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can tailor your Irwin escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Irwin?

Secure incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Irwin break.

How to plan a trip to Irwin?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Irwin.
  2. Set a budget: Factor in expenses such as flights, transportation and food when working out how much to set aside for your trip to Irwin. Then, select a property that matches your budget, whether that's a wallet-friendly stay or a lavish getaway.
  3. Decide how long to go for: Now that you're more familiar with Irwin, you can work out the ideal length of your break. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find an Irwin vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.