A nighttime cityscape with illuminated skyscrapers and a prominent clock tower.

Rush Street Romantic 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 Romantic holiday packages in Rush Street

Price found within the past 48 hours. Click for updated prices.
  • 29 Dec - 3 Jan

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.4/10 - Very good (3,186 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,271
    €1,046
    per traveller
    found 5 hours ago
    Hotel Felix River North/Magnificent Mile
  • 29 Dec - 3 Jan

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (2,413 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,472
    €1,113
    per traveller
    found 5 hours ago
    Hotel Saint Clair- Magnificent Mile
  • 29 Dec - 3 Jan

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,585 reviews)
    "LOVE this hotel! Location is perfect and you can walk everywhere! Just wished they had a pool"
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,507
    €1,213
    per traveller
    found 5 hours ago
    Swissotel - Chicago
  • 29 Dec - 3 Jan

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,541 reviews)
    "Very clean and comfortable. Valet was helpful and kind"
    Reviewed November 13, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,367
    €1,116
    per traveller
    found 5 hours ago
    Sports Illustrated Resorts Chicago
  • 29 Dec - 3 Jan

    InterContinental Chicago Magnificent Mile by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.2/10 - Wonderful (3,427 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,399
    €1,159
    per traveller
    found 5 hours ago
    InterContinental Chicago Magnificent Mile by IHG

Frequently Asked Questions

How much does a Rush Street holiday package cost?

Our Rush Street holiday packages, which start from as low as €1,046, are the perfect way to save loads of cash. Pick your favourite hotels, flights and more to create your perfect escape.

How do I get a cheap travel package to Rush Street?

Combine your bookings with Expedia to save big on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your Rush Street holiday package can be customized exactly to suit your travel style. With all that extra money, why not include one or two exciting activities and tours? It's an easy way to unlock even more savings. That dream holiday to Rush Street is much closer than you thought!

Where should I stay in Rush Street?

Travellers come from all over to experience McCormick Place and Millennium Park in Rush Street. Book a hotel close to these popular attractions and visit them at your leisure.

What are the top hotels in Rush Street?

Thompson Chicago, part of Hyatt is one of Rush Street's leading hotels. Reserve a room here and you can sleep soundly knowing you're in good hands.

How far in advance should I book my Rush Street holiday?

Search Expedia to compare international airfares as soon as you know your travel dates. You can normally purchase a seat up to a year before departure. If you don't see your preferred air carrier, or you have to book last minute, fear not. Cheap tickets to Rush Street sometimes appear just weeks before departure.

What does an Expedia Rush Street travel package include?

With Expedia, you can choose a combination of car rentals, hotels and flights to build your perfect Rush Street travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Don't forget, the more you bundle, the more deals you'll score!

What should I know before booking a Rush Street travel package?

Bundling your bookings into a Rush Street holiday package is the easiest way to organise your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?

Can I choose my airline with a Rush Street Expedia holiday package?

Definitely. Expedia has more than 550 partner airlines to pick from worldwide. With so much choice, finding the ideal carrier to bring you to Rush Street won't be hard.

If I'm not able to travel, can I cancel my Rush Street holiday package?

Whether it's your hotel or flight, you can cancel and rebook it. Locked in your Rush Street holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. If it's been longer than that, you may be charged a fee by your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We'll help you every step of the way.