Esmond Vacations from $329
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Esmond Vacation Packages
- Holiday Inn & Suites Chicago - Downtown by IHG
Dec 25 - Dec 30Holiday Inn & Suites Chicago - Downtown by IHG + Flight
Downtown Chicago5 nights3.0 star property8.6/10 - Excellent (1,274 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$477$329found 1 day agoper traveler - Pendry Chicago
Dec 25 - Dec 30Pendry Chicago + Flight
Downtown Chicago5 nights4.5 star property9.2/10 - Wonderful (1,164 reviews)"The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."Reviewed November 8, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$997$611found 1 day agoper traveler - Level Chicago Fulton Market
Jan 23 - Jan 27Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (609 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$911$575found 1 day agoper traveler - The Emily Hotel
Jan 23 - Jan 27The Emily Hotel + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (1,357 reviews)"The location of this hotel is great with the exception of its proximity to the train tracks. There were train horns sounding at all hours and fairly frequently. The hot water in my room took an extremely long time and house keeping didn’t always replenish/ replace items they would remove such as dark face cloth for makeup removal and wet makeup removal towelette."Reviewed November 10, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$1,089$725found 1 day agoper traveler - Hilton Grand Vacations Club Chicago Magnificent Mile
Dec 25 - Dec 30Hilton Grand Vacations Club Chicago Magnificent Mile + Flight
Downtown Chicago5 nights3.5 star property9.2/10 - Wonderful (485 reviews)"El servicio increíble, todo estaba limpio y el personal muy amable"Reviewed November 9, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$603$414found 1 day agoper traveler
Esmond Hotel Deals
Best Western Rochelle Inn & Suites near DeKalb
Best Western Rochelle Inn & Suites near DeKalb
"Windows were very dirty Very difficult to see out Made room look not well kept Like to let morning light to fill room!!"
"😁 everything was good"
Holiday Inn Express Rochelle by IHG
Holiday Inn Express Rochelle by IHG
"Clean nice hotel with really great breakfast"
Comfort Inn DeKalb - University Area
Comfort Inn DeKalb - University AreaFrequently Asked Questions
How much does an Esmond vacation package cost?
Offering great value package deals from $329 on Expedia, you'll be pleasantly surprised at how much a vacation to Esmond costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Esmond?
March, November and December are the best times to search for cheap Esmond vacation packages. Opting to travel in quieter months means you can generally find reduced prices on flights and accommodations.
How many days is enough for Esmond?
The ideal duration of your Esmond vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to tick off all the major attractions and explore some hidden spots along the way.
How to find the best Esmond package deals?
Finding a cheap Esmond package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Esmond package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Esmond vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging stays and flights individually. Better still, you can tailor your Esmond getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Esmond?
If you're planning a spur-of-the-moment Esmond vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Esmond vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Esmond trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.