A city skyline with high-rise buildings, a marina with boats, and a river.

Cicero 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 Cicero flight + hotel deals

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 (3,187 reviews)
    "Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours."
    Reviewed November 14, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,271
    €1,046
    per traveller
    found 6 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 (2,414 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,472
    €1,113
    per traveller
    found 6 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 6 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 6 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 (3,428 reviews)
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,399
    €1,159
    per traveller
    found 6 hours ago
    InterContinental Chicago Magnificent Mile by IHG

Discover the most popular places to visit in Cicero

Cicero 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 a Cicero holiday package cost?

Offering great value package deals from €1,046 on Expedia, you'll be pleasantly surprised at how much a holiday to Cicero costs! Expedia's packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Cicero?

You can typically find lower prices and greater availability in January, February and November. Browse our cheap Cicero holiday packages and you could get some excellent off-season deals.

How many days is enough for Cicero?

The ideal duration of your Cicero holiday depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to go to all the top attractions and discover some hidden treasures along the way.

How to find the best Cicero package deals?

Begin your search for a Cicero package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Cicero package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Cicero getaway off to a flying start.

Is it cheaper to book a Cicero holiday as a package?

Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalised Cicero holiday by choosing your preferred airline, accommodation type and car class.

When to book a holiday package to Cicero?

If you're planning an impromptu Cicero holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.

How to plan a trip to Cicero?

  1. Choose when to go: Check your schedule and get your bags packed. Your favourite time of year and the available activities will also help you decide when to escape to Cicero.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to save for your trip to Cicero. Then, select a hotel that fits your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Decide how long to go away for: Now that you're up to speed on Cicero, you can figure out the ideal length of your holiday. Put together a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Cicero holiday package that brings all your bookings together.

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