Esmond Vacation Packages
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Top Esmond vacation deals
Price found within the past 48 hours. Click for updated prices.
- The Whitehall Hotel, BW Premier Collection
Sept 25 - Sept 28The Whitehall Hotel, BW Premier Collection + Flight
Downtown Chicago3 nights3.5 star property8.4/10 - Very good (3,931 reviews)"The hotel was amazing. The staff was amazing. I was able to walk around and get to everywhere that I needed to go. It was in a perfect area, and I would definitely recommend it to anyone who wanted to stay."Reviewed July 31, 2026Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $1,099CA $796found 2 days agoper traveller - Hotel Riu Plaza Chicago
Sept 25 - Sept 28Hotel Riu Plaza Chicago + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (4,879 reviews)"What a treat the buffet breakfast was! We didn’t have to leave the property to have a delicious breakfast and coffee! Service at the property was top notch!"Reviewed July 31, 2026Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $1,699CA $1,089found 2 days agoper traveller - Level Chicago Fulton Market
Aug 30 - Sept 3Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (542 reviews)"Comes with all the comforts of Home."Reviewed July 29, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,522CA $1,074found 2 days agoper traveller - Hotel Saint Clair- Magnificent Mile
Sept 25 - Sept 28Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.4/10 - Very good (2,073 reviews)"Enjoyed the stay"Reviewed July 31, 2026Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $1,205CA $854found 2 days agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
Sept 25 - Sept 28Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights4.0 star property9.4/10 - Exceptional (2,623 reviews)"This was our second time here and it was still very good! The staff is awesome!"Reviewed July 31, 2026Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $1,489CA $1,090found 2 days agoper traveller
Esmond Hotel Deals
8.2 out of 10, Very good, (1,002 reviews)
8.2/10
Very good
(1,002 reviews)
"Excellent stay,soft comfy beds,very clean property and it was quiet so very quiet. They were always cleaning or sweeping to maintain cleanliness and ground!!! Would stay at again."
The price is CA $93
CA $93
CA $103 total
includes taxes & fees
Aug 4 - Aug 5
Best Western Rochelle Inn & Suites near DeKalb
Best Western Rochelle Inn & Suites near DeKalb2.5 star property
15.4 km from Esmond
8.0 out of 10, Very good, (513 reviews)
8.0/10
Very good
(513 reviews)
"Did not care for the property. Thought I was booking a Comfort Suites but it changed to a Best Western . The room was old and had a funny smell like a ash tray. It didn't feel clean. Would definitely not stay there again."
The price is CA $106
CA $106
CA $118 total
includes taxes & fees
Aug 12 - Aug 13
Holiday Inn Express Rochelle by IHG
Holiday Inn Express Rochelle by IHG2.5 star property
13.5 km from Esmond
8.6 out of 10, Excellent, (442 reviews)
8.6/10
Excellent
(442 reviews)
"Clean room with comfortable beds. Tasty breakfast and cold AC. Get the suite upgrade. It's worth it."
The price is CA $139
CA $139
CA $154 total
includes taxes & fees
Aug 30 - Aug 31
6.8 out of 10, (448 reviews)
6.8/10
(448 reviews)
"TV was great"
The price is CA $95
CA $95
CA $105 total
includes taxes & fees
Aug 30 - Aug 31
Country Inn & Suites by Radisson, Sycamore, IL
Country Inn & Suites by Radisson, Sycamore, IL2.5 star property
19.7 km from Esmond
8.4 out of 10, Very good, (1,000 reviews)
8.4/10
Very good
(1,000 reviews)
"Toilet ran all night and hair dryer didn’t work, pool was under renovation. Room was well laid out and very clean"
The price is CA $123
CA $123
CA $136 total
includes taxes & fees
Aug 30 - Aug 31
9.4 out of 10, Exceptional, (1,000 reviews)
9.4/10
Exceptional
(1,000 reviews)
The price is CA $182
CA $182
CA $207 total
includes taxes & fees
Aug 30 - Aug 31
Comfort Inn DeKalb - University Area
Comfort Inn DeKalb - University Area2.5 star property
17.3 km from Esmond
7.2 out of 10, Good, (329 reviews)
7.2/10
Good
(329 reviews)
"."
The price is CA $112
CA $112
CA $127 total
includes taxes & fees
Aug 30 - Aug 31
7.6 out of 10, Good, (613 reviews)
7.6/10
Good
(613 reviews)
"Pool was not working. Railing for hot tub was so low, I could not enter it safely. Lock didn’t work on back door. Very low water pressure. Needs a whole update."
The price is CA $101
CA $101
CA $112 total
includes taxes & fees
Aug 16 - Aug 17
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.
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 Esmond vacation package cost?
Offering great value package deals from CA $796 on Expedia, you'll be thrilled with how little a vacation to Esmond costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Esmond?
You can generally find reduced prices and better availability in January, February and April. Check out our cheap Esmond vacation packages and you could score some great off-season discounts.
How many days is enough for Esmond?
Generally, a handful of days is enough to tick off the major attractions during your Esmond vacation. But if you want to have more time to chill out or take day trips, consider extending your trip.
How to find the best Esmond package deals?
Use Expedia's filter tool to find some of the best Esmond package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Esmond package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book an Esmond vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking hotels and flights individually. Better still, you can personalize your Esmond escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Esmond?
Enjoy incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Esmond vacation.
How to plan a trip to Esmond?
- Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Esmond.
- Set your budget: Consider expenses like flights, food and transportation when working out how much to set aside for your trip to Esmond. Then, pick a property that works with your budget, whether that's an economical option or a deluxe getaway.
- Determine how many days away: Start by listing all the activities and attractions you want to experience in Esmond. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your airfare and accommodations: Once you've nailed down your travel dates and duration, book the perfect Esmond vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.