Esmond Holidays from £720

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to £750 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Top Esmond flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 20 Jan - 24 Jan

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,007 reviews)
    "I was surprised by the $29.50 daily charge for "Guest Amenity Fee". I did not ask for it. I don't even know what it is. I hate when hotels charge you hidden items."
    Reviewed November 9, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £898
    £720
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,082 reviews)
    "Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨"
    Reviewed November 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,797
    £1,324
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 20 Jan - 24 Jan

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - 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, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,091
    £819
    per traveller
    found 1 day ago
    Pendry Chicago
  • 20 Jan - 24 Jan

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,310 reviews)
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,202
    £956
    per traveller
    found 1 day ago
    Viceroy Chicago
  • 25 Dec - 30 Dec

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,902 reviews)
    "Upon arrival we were greeted immediately. The staff helped us unload our bags into a luggage cart and valet took the car to park. Our room was available for early check in. We stayed in the 7th floor in a single king room. Everything was clean and the views were great. We went up to the 22nd floor to see the river views from the rooftop bar. This hotel is in an absolute perfect location to see Chicago. You are close enough to walk to river walk, millennium park, the train, and magnificent mile...."
    Reviewed November 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,021
    £827
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

Esmond 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 Esmond travel package cost?

Get ready to book, because a getaway to Esmond starts from only £720. When you bundle your flights, hotels and car rentals into a travel package, you'll pick up the best bargains.

If I'm not able to travel, can I cancel my Esmond travel package?

It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Esmond travel package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

How do I get a cheap travel package to Esmond?

Our Esmond travel packages mean plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and extras (including activities) into a budget-friendly package. But great bargains are just the beginning of your next epic adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotel options worldwide to pick from. Whatever your style, there's a package that's perfect for you.

Does Expedia offer Book Now, Pay Later Esmond holidays?

Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can escape on that well-deserved holiday now.
  • Pay in instalments holidays: If you want to pay off your escape in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Hitting the "book now" button is easier with this payment option. Simply put down a small deposit on your booking and then start packing your suitcase.

What are the top hotels in Esmond?

Book a stay at Hyatt Regency Chicago. It's one of the area's most popular hotels. Another top-rated option in Esmond is The Godfrey Hotel Chicago.

How far in advance should I book my Esmond holiday?

To bag rock-bottom prices, book early. Airlines generally advertise flight tickets, along with some of the lowest fares, around a year ahead of time. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway to Esmond, there are always plenty of great deals on Expedia. Book something in today!

What does an Expedia Esmond travel package include?

Hotels, flights and rental cars — we've got them covered. With Expedia, you can create your Esmond package just the way you want. All you have to do is work out just what you need. Once you've made your booking, you can add on fun things like tours and activities. The more you bundle, the more you save!

What should I know before booking an Esmond travel package?

So many places to wander around, so many things to see. With a package, you'll be able to tick more of them off your list. Combine your flights, rental cars and hotels and see how much you save.

Can I choose my airline with an Esmond Expedia travel package?

You can, and with over 550 airlines to choose from around the world, it's all about choice. Search the available options and see which airline best fits your budget and needs.

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