Cicero Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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 hotels in Cicero

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is S$278 per night from 6 Aug to 7 Aug
S$278
6 Aug - 7 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$298 per night from 3 Aug to 4 Aug
S$298
3 Aug - 4 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$459 per night from 9 Aug to 10 Aug
S$459
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,930 reviews)
"Why book here? LOCATION and competitive price. Why not? If you care about hospitality. This isn't going to be the place. Some of the front desk staff were impatient and border line dismissive. No decaf, despite a sign saying it was available. Just plan to go to Starbucks about a block away for coffee ..."

Reviewed on 18 Jul, 2026

The Wade
See all 4,730 properties in Cicero
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.

Stay near popular Cicero attractions

Hawthorne Works Museum

This intimate museum chronicles the groundbreaking Hawthorne Studies and Western Electric's industrial legacy. Explore recreated factory floors and discover how workplace psychology was forever changed here.
See properties

What to do in Cicero

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$52
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Cicero

Frequently asked questions

How much does a Cicero holiday package cost?
Offering great value package deals 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.