Streeterville Holidays from AU$2,187

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Your Streeterville Holiday

Experience the best that Streeterville has to offer with a Streeterville holiday package. From its families and history to its culture and more, you'll quickly be won over by this lakeside neighbourhood. Wondering what to see and do during your trip to Streeterville? Nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago are excellent places to start. Don't just wish for it — turn it into reality! Lock in your perfect Streeterville holiday with Expedia and experience travel your way.

Top Holiday Package Deals in Streeterville

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$2,900, price is now AU$2,187 per person
AU$2,187
per person
14 Mar - 18 Mar
found 4 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
The hotel was located in a great spot central to many places. The room was cold. Temp read 62 despite trying to set thermostat to 71.

Reviewed on 23 Dec 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$3,253, price is now AU$2,294 per person
AU$2,294
per person
14 Mar - 18 Mar
found 4 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amazing close to Michigan Ave

Reviewed on 24 Dec 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,168, price is now AU$2,363 per person
AU$2,363
per person
14 Mar - 18 Mar
found 4 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
While the front desk staff could be more welcoming, the bell desk staff was very nice and offered water to those waiting

Reviewed on 24 Dec 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$3,289, price is now AU$2,457 per person
AU$2,457
per person
14 Mar - 18 Mar
found 4 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Clean and great location

Reviewed on 24 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was AU$3,480, price is now AU$2,627 per person
AU$2,627
per person
14 Mar - 18 Mar
found 4 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec 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 AU$157 per night from 5 Jan to 6 Jan
AU$157
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,551 reviews)
Room was warm Recommend softer toilet paper please

Reviewed on 23 Dec 2025

Hilton Chicago/Magnificent Mile Suites
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 6 Jan to 7 Jan
AU$134
6 Jan - 7 Jan 2026
includes taxes & fees
8.2/10 Very Good! (3,783 reviews)
The room in general was very clean, with the exception of the bathroom, where I saw several hairs in the toilet and bathtub. Also, when we turned on the heating, it was extremely noisy; we had to turn it off to sleep.

Reviewed on 18 Dec 2025

The Whitehall Hotel, BW Premier Collection
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
900 E Grand Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 20 Jan to 21 Jan
AU$202
20 Jan - 21 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (2,270 reviews)
The room was beautiful & perfect & the staff was very welcoming everything was perfect 10/10 highly recommend

Reviewed on 19 Dec 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
See all 4,689 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.
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Frequently asked questions

How much does a Streeterville holiday package cost?
Maybe less than you might think — from as low as AU$2,187, 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 acclaimed art galleries.

875 North Michigan Avenue

360 CHICAGO

You can learn about the history of Chicago with a visit to 360 CHICAGO. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

360 CHICAGO

Activities

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$61
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$67
per adult
92% of travellers recommend
Chicago Crime and Mob Bus 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.