Hooppole 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 Hooppole Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,080, price is now CA $773 per person
CA $773
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was CA $1,341, price is now CA $834 per person
CA $834
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
The staff is very friendly and professional.

Reviewed on Oct 27, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,554, price is now CA $1,036 per person
CA $1,036
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Great location, amenities and wonderful staff.

Reviewed on Oct 27, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,749, price is now CA $1,169 per person
CA $1,169
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Price was CA $1,400, price is now CA $1,010 per person
CA $1,010
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,348 reviews)
No amenities. Only 2 pillows. The room is like a cell. Unable to check us in on time, about 1 1/2 hours past check in. Staff didn't offer anything like breakfast or drink at bar for inconvenience. The only good thing was location.

Reviewed on Oct 27, 2026

Ready to book your vacation to Hooppole?

 

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Hooppole Hotel Deals

Best Western Geneseo Inn

Best Western Geneseo Inn

2.5 out of 5
1375 S Oakwood Avenue Geneseo IL
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Nov 10 to Nov 11
CA $147
CA $163 total
Nov 10 - Nov 11
includes taxes & fees
Best Western Geneseo Inn
Best Western Annawan Inn

Best Western Annawan Inn

2.5 out of 5
315 Canal Street Annawan IL
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Nov 3 to Nov 4
CA $129
CA $144 total
Nov 3 - Nov 4
includes taxes & fees
Best Western Annawan Inn
Regency Inn Geneseo

Regency Inn Geneseo

2 out of 5
765 West Main Street Geneseo IL
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from Nov 1 to Nov 2
CA $91
CA $101 total
Nov 1 - Nov 2
includes taxes & fees
7.8/10 Good! (468 reviews)
"Clean, quiet, the staff were nice, and it’s reasonably priced. That’s all a really need."

Reviewed on Oct 19, 2026

Regency Inn Geneseo
See all 11 properties in Hooppole
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Hooppole vacation package cost?
Offering great value package deals from CA $773 on Expedia, you'll be surprised at how little a vacation to Hooppole costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Hooppole?
January, February and April are the best times to search for cheap Hooppole vacation packages. Travelling in quieter months means you can generally find reduced prices on flights and hotels.
How many days is enough for Hooppole?
Usually, a handful of days is enough to see the top attractions during your Hooppole vacation. However, if you'd like to have some time to kick back or go on day tours, consider extending your trip.
How to find the best Hooppole package deals?
Start your search for a Hooppole package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Hooppole package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hooppole adventure off to a flying start.
Is it cheaper to book a Hooppole vacation as a package?
You can enjoy significant savings on your Hooppole retreat by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Hooppole?
If you're planning a spur-of-the-moment Hooppole vacation, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Hooppole?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Hooppole.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Hooppole.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Hooppole. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Hooppole 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.