Streeterville Holidays from NZ$2,859
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Top Holiday Package Deals in Streeterville
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$5,454, price is now NZ$3,814 per person
NZ$3,814
per person
30 Oct - 4 Nov
found 3 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on 8 Sep. 2025
The Emily Hotel
Downtown Chicago
Price was NZ$4,112, price is now NZ$3,090 per person
NZ$3,090
per person
30 Oct - 4 Nov
found 3 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on 8 Sep. 2025
Pendry Chicago
Downtown Chicago
Price was NZ$4,061, price is now NZ$3,181 per person
NZ$3,181
per person
30 Oct - 4 Nov
found 3 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend
Reviewed on 8 Sep. 2025
Our guide on where to stay in Streeterville
Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Our pick of the best Streeterville Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$317 per night from 22 Sept to 23 Sept
NZ$317
22 Sept - 23 Sept
includes taxes & fees
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
201 East Walton Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$330 per night from 2 Oct to 3 Oct
NZ$330
2 Oct - 3 Oct
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$330 per night from 22 Sept to 23 Sept
NZ$330
22 Sept - 23 Sept
includes taxes & fees
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
Discover the most popular places to visit in Streeterville
Water Tower Place
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
John Hancock Center
You can find out about the history of Chicago when you stop by John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.
Broadway Playhouse
You can make plans for a show at Broadway Playhouse during your stay in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
Activities
Wendella's 90-min Chicago River Architecture Tour
NZ$76
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
