Streeterville Holidays from NZ$3,128

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Top Holiday Package Deals in Streeterville

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (397 reviews)
Wonderful hotel right downtown. Could walk to stores and restaurants. Lovely breakfast

Reviewed on 9 Apr. 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (24 reviews)
Parking is difficult. Closest designated spot was 2 blocks away. Booking was easy enough but communication between site and accommodation was inefficient. Email was not passed on for final access instructions to unmanned accommodation site. The finalisation process did not allow for visitors with International phone numbers to be contacted directly either. Login does not accept driver's licence picture.

Reviewed on 28 Apr. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
The staff wasn’t very welcoming. After booking, they send you a form asking for almost everything except your social security number. I understand it’s for the safety of the residents, but I didn’t feel comfortable providing that much information. It felt like I had no choice but to go through with it since I wouldn’t get my money back otherwise. The walls are also extremely thin; you can hear everything. One of the neighbors blasted music from 6 PM until 1 AM on a Tuesday. They only turned it down after I reported it. Overall, I wouldn’t stay here again.

Reviewed on 30 Apr. 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,465 reviews)
Loved the location, the best roof top in Chicago!

Reviewed on 27 Apr. 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
12 Jul - 18 Jul
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Love the rooftop! You get a beautiful view of the city.

Reviewed on 30 Apr. 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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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$318 per night from 8 May to 9 May
NZ$318
includes taxes & fees
8 May - 9 May
"Pool and fitness center was not in service."

Reviewed on 28 Apr. 2025

Hilton Chicago/Magnificent Mile Suites
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent Mile
3 out of 5
165 East Ontario Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$277 per night from 11 May to 12 May
NZ$277
includes taxes & fees
11 May - 12 May
8.8/10 Excellent! (1,334 reviews)
"Hotel is greatly located close to everything, the variety of dinning options, the shopping, you can walk everywhere. Staff is friendly and rooms are clean, ample and quiet. Breakfast is not included but the restaurant is ok. Overall I like it."

Reviewed on 27 Apr. 2025

Courtyard by Marriott Chicago Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4 out of 5
300 E Ohio St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$283 per night from 11 May to 12 May
NZ$283
includes taxes & fees
11 May - 12 May
8.8/10 Excellent! (1,838 reviews)
"It was a great stay and walking distance to everything"

Reviewed on 29 Apr. 2025

DoubleTree by Hilton Chicago - Magnificent Mile
See all 4,140 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$3,128, 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

4.5/5(16 reviews)

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

Water Tower Place
John Hancock Center

John Hancock Center

4.5/5(36 reviews)

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.

John Hancock Center

Broadway Playhouse

You can make plans for a show at Broadway Playhouse during your stay in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Broadway Playhouse

Activities

Flyover in Chicago

Flyover in Chicago

NZ$64
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

NZ$82
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$61
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.