Chicago Holiday Deals

Choose two or more items and save on your trip:

Top Chicago holiday deals

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$2,620, price is now NZ$2,216 per person
NZ$2,216
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was NZ$2,690, price is now NZ$2,263 per person
NZ$2,263
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was NZ$2,774, price is now NZ$2,360 per person
NZ$2,360
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
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$2,619, price is now NZ$2,262 per person
NZ$2,262
per person
22 Dec - 27 Dec
found 9 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Top hotels for your Chicago holiday

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$211 per night from 7 Dec to 8 Dec
NZ$211
7 Dec - 8 Dec
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Room was fine. Check in was not good. Front desk not helpful

Reviewed on 9 Nov 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 8 Dec to 9 Dec
NZ$225
8 Dec - 9 Dec
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Amazing Hotel, Quality,, Food and Service. Best place location wise as well.

Reviewed on 6 Nov 2025

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
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$242 per night from 19 Nov to 20 Nov
NZ$242
19 Nov - 20 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
It was ok

Reviewed on 7 Nov 2025

Opens in a new windowCongress Plaza Hotel
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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.

Popular places to visit

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and a city

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

With a visit to Navy Pier, a favourite shopping spot in Chicago, you can search for that perfect souvenir. Amble around this vibrant area's lakeside or experience its fascinating museums.

Navy Pier

^Savings based on all package bookings made with Flight + Hotel on lastminute.co.nz from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.