Streeterville Holidays from AU$1,980

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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.
Super 8 by Wyndham Bridgeview/Chicago Area

Super 8 by Wyndham Bridgeview/Chicago Area

2 out of 5
per person
23 Oct - 27 Oct
found 12 hours ago
Return direct flight included
Perth (PER) to Chicago (ORD)
7.4/10 Good! (1,016 reviews)
Quiet clean convenient

Reviewed on 3 Aug. 2025

Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
per person
23 Oct - 27 Oct
found 12 hours ago
Return direct flight included
Perth (PER) to Chicago (MDW)
8.2/10 Very Good! (1,020 reviews)
I would recommend this hotel for a one- or two-night stay. It’s suitable for short visits but may not be ideal for a longer stay.

Reviewed on 4 Aug. 2025

Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

2.5 out of 5
per person
23 Oct - 27 Oct
found 12 hours ago
Return direct flight included
Perth (PER) to Chicago (CHI)
8.2/10 Very Good! (1,001 reviews)
Good location, great breakfast choices. Pool and hot tub needs a little TLC.

Reviewed on 5 Aug. 2025

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
per person
23 Oct - 27 Oct
found 12 hours ago
Return direct flight included
Perth (PER) to Chicago (ORD)
8.4/10 Very Good! (526 reviews)
I thought I was getting a super deal here based on all the high reviews that Expedia had listed but i'm getting the suspicion that these were all posted by employees. A rating of 8.4 /10 is way too high, buoyed up by a bunch of 10/10. I'm more in the 6/10 range. The carpet was worn, the tub was beat up, the ice machines were always broken, it is definitely in need of a deep clean and a refresh. Staff was nice and breakfast was decent, bed was comfortable enough. Just realize this is a basic hotel and that is all you should expect.

Reviewed on 31 Jul. 2025

Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
per person
23 Oct - 27 Oct
found 12 hours ago
Return direct flight included
Perth (PER) to Chicago (ORD)
8.2/10 Very Good! (1,007 reviews)
Staff excellent. Room was huge and clean. Bed good. Pillows were TERRIBLE. Quiet. Great breakfast. Hallways filled with what looked like plaster…maybe from remodel so can forgive that. So close to family I visit. Water pressure great. Nice towels.

Reviewed on 3 Aug. 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$261 per night from 17 Aug to 18 Aug
AU$261
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,559 reviews)
"Location was in walking distance to restaurants and close to attractions"

Reviewed on 2 Aug. 2025

Hilton Chicago/Magnificent Mile Suites
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 1 Sept to 2 Sept
AU$216
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,152 reviews)
Almost Perfect
"The staff is wonderful. Everyone is very attentive to customer needs. The room was just spacious enough. The beds were comfortable. I love a hotel that provides bottles of water in the room at no additional cost. I have only two minor complaints. First, there was only one bar of soap provided. We ..."

Reviewed on 4 Aug. 2025

The Wade
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$217 per night from 2 Sept to 3 Sept
AU$217
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (3,511 reviews)
"Perfect location for our stay. Breakfast was good and sort of a bonus for a hotel in downtown Chicago. Good variety of breakfast options.The room was quiet and the bed and pillows comfortable. Would definitely consider staying there on a future trip to Chicago."

Reviewed on 2 Aug. 2025

The Whitehall Hotel, BW Premier Collection
See all 4,568 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.
All Inclusive Holidays
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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$1,980, 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
John Hancock Center

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 acclaimed theatre scene.

John Hancock Center

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 entertainment choices.

360 CHICAGO

Activities

River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

AU$46
per adult
92% of travellers recommend
Skyline Lake Tour
Chicago White Sox Baseball Game at Guaranteed Rate Field

Chicago White Sox Baseball Game at Guaranteed Rate Field

AU$31
per adult
Chicago White Sox Baseball Game at Guaranteed Rate Field
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.