Streeterville Holidays from NZ$2,216

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Top Holiday Package Deals in Streeterville

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 15 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
A+++ in all areas. And fabulous location.

Reviewed on 6 Nov 2025

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 15 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
Friendly, clean; delightful stay.

Reviewed on 7 Nov 2025

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 15 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,013 reviews)
Amenities, staff, and room

Reviewed on 9 Nov 2025

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 15 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
It was a beautiful room with an absolutely gorgeous view. The staff was friendly and helpful.

Reviewed on 5 Nov 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 featuring a city

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.

Find hotels in Downtown Chicago

Our pick of the best Streeterville Hotel Deals

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
8.8/10 Excellent! (3,243 reviews)
Large, clean spacious rooms. Convenient to shopping and restaurants. A very good bargain for the price.

Reviewed on 8 Nov 2025

Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 8 Dec to 9 Dec
NZ$266
8 Dec - 9 Dec
includes taxes & fees
9.2/10 Wonderful! (2,731 reviews)
Breakfast. Delish Cushy pillows. Comfy bed Nice shower Staff so friendly and helpful.

Reviewed on 7 Nov 2025

Hotel Riu Plaza Chicago
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$204 per night from 26 Nov to 27 Nov
NZ$204
26 Nov - 27 Nov
includes taxes & fees
8.4/10 Very Good! (2,884 reviews)
I booked city view room but got 10th floor room with no view

Reviewed on 8 Nov 2025

Aloft Chicago Mag Mile
See all 4,581 properties in Streeterville
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 Streeterville holiday package cost?
Maybe less than you might think — from as low as NZ$2,216, in fact! By bundling hotels, flights and car rentals into a custom-built holiday package, your Streeterville escape is just clicks away.
How do I get a cheap travel package to Streeterville?
Combine your flight and hotel bookings, throw in extras such as a rental car or activities, and save with a Streeterville holiday package. You won't just pick up amazing discounts on your adventure — you'll have loads of choice at your fingertips too. When you book through Expedia, you'll have your pick of over 550 partner airlines and 1 000 000 hotels throughout the world. Your dream holiday starts right here, right now!
Where should I stay in Streeterville?
Most people who travel to Streeterville include both McCormick Place and Millennium Park on their must-see lists. Why not reserve a hotel near these main attractions?
What are the top hotels in Streeterville?
Make a reservation at Sable at Navy Pier Chicago, Curio Collection by Hilton. It's one of the neighbourhood's most in-demand hotels. Another well-known option in Streeterville is Omni Chicago Hotel.
How far in advance should I book my Streeterville holiday?
Travellers are usually able to browse international flights on Expedia up to 12 months prior to departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Streeterville travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to crafting your Streeterville getaway, you're in charge!
What should I know before booking a Streeterville travel package?
Booking all the parts of your getaway together is one of the easiest ways to save. Bundle your car rentals, airfares and hotels into a neat package. But you're not restricted to hotels. Expedia offers all sorts of properties, including holiday homes such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Streeterville Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just select the carrier you want and create your ideal Streeterville holiday.
If I'm not able to travel, can I cancel my Streeterville holiday package?
Yes you can, and we're here to help. You may be able to cancel or amend your Streeterville holiday package for free if you booked in the last 24 hours. However, you may be charged a fee by your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, browse our Customer Service Portal for more information.

Discover the most popular places to visit in Streeterville

Water Tower Place

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
875 North Michigan Avenue

875 North Michigan Avenue

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.

875 North Michigan Avenue

Broadway Playhouse

You can make plans for a show at Broadway Playhouse during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Broadway Playhouse

Activities

River tour boat in Chicago

Architecture River Tour

NZ$85
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.