A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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 Luxury holiday packages in Northwest Side

Price found within the past 48 hours. Click for updated prices.
  • 17 Dec - 21 Dec

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.4/10 - Very good (3,177 reviews)
    "I stayed for a night before transferring to the main hotel while there for chicago marathon. Room was a little small but I was okay with given the price. Just know the standard rooms can be a little tight so don't be afraid to upgrade if you have lots of luggage."
    Reviewed November 10, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €913
    €785
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • 17 Dec - 21 Dec

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,584 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,139
    €931
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • 17 Dec - 21 Dec

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,903 reviews)
    "ubicacion perfecta"
    Reviewed November 10, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,172
    €968
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • 17 Dec - 21 Dec

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (197 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,046
    €864
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • 17 Dec - 21 Dec

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,397 reviews)
    "Clean Hotel, but Disappointing Customer Service I’ve stayed at this hotel multiple times while traveling to Chicago for classes. While the hotel is clean and conveniently located, the inconsistent customer service has been disappointing. During an earlier stay, I asked for bottled water and was directed to paid vending machines. Later, I noticed other guests receiving complimentary water at check-in. When I asked during subsequent stays, I received it too. While minor, this reflects the..."
    Reviewed November 10, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €986
    €827
    per traveller
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile

Discover the most popular places to visit in Northwest Side

Frequently Asked Questions

How much does a Northwest Side holiday package cost?

Explore the best of Northwest Side from just €785. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.

How do I get a cheap travel package to Northwest Side?

Book everything all in one place with our Northwest Side holiday packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to choose from, you'll have the flexibility to mix and match as you like.

How far in advance should I book my Northwest Side holiday?

Savvy travellers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Low prices occasionally become available just weeks prior to departure.

What does an Expedia Northwest Side travel package include?

Hotels, rental cars and flights, or any combination of the three — you decide! Whether you're headed to Northwest Side on a family road trip or travelling solo, there's a package to fit every budget and style. Once you've made your booking, why not add on some activities?

Can I choose my airline with a Northwest Side Expedia holiday package?

Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flights, hotels and activities that suit you.

If I'm not able to travel, can I cancel my Northwest Side holiday package?

Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.