Cicero Holidays from NZ$3,873

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The Latest Cicero Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$4,297, price is now NZ$3,873 per person
NZ$3,873
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Excellente

Reviewed on 1 July 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was NZ$6,663, price is now NZ$5,321 per person
NZ$5,321
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Great location in what feels like the heart of the city, just steps from the lakefront, excellent restaurants, and many attractions. The staff were warm, welcoming, and always courteous. There were a few occasions when requests took a little longer than expected or communication was a bit challenging. It would be wonderful if there were additional ways to contact the staff besides the traditional in-room phone, as that would make the experience even more convenient. I didn't have a chance to try the breakfast, but one feature I really appreciated was the direct connection on the sixth floor to a charming modern shopping mall, where it's easy to grab a quick meal, coffee, or drinks.

Reviewed on 1 July 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,435, price is now NZ$3,900 per person
NZ$3,900
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Very nice hotel. Great location, nice sized rooms.

Reviewed on 2 July 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was NZ$4,523, price is now NZ$3,985 per person
NZ$3,985
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on 1 July 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was NZ$5,044, price is now NZ$4,520 per person
NZ$4,520
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
Palmerston North (PMR) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.

Reviewed on 1 July 2026

Cicero Holiday

Our pick of the best Cicero Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$254 per night from 7 July to 8 July
NZ$254
7 July - 8 July
includes taxes & fees
8/10 Very good! (10,189 reviews)
"Lugar limpio, buenas ubicación"

Reviewed on 1 July 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 5 July to 6 July
NZ$379
5 July - 6 July
includes taxes & fees
9.2/10 Wonderful! (1,828 reviews)
"Very nice hotel. Great location, nice sized rooms."

Reviewed on 2 July 2026

Omni Chicago Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$396 per night from 6 July to 7 July
NZ$396
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (4,478 reviews)
"R"

Reviewed on 2 July 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,811 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

NZ$41
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$68
per adult
92% of travellers recommend
Art Institute of Chicago
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$78
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Cicero

Frequently asked questions

How much does a Cicero holiday package cost?
Offering great value package deals from NZ$3,873 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.