Streeterville Holidays from AU$4,460

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$4,903, price is now AU$4,460 per person
AU$4,460
per person
5 Jan - 11 Jan
found 1 hour ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was AU$5,255, price is now AU$4,702 per person
AU$4,702
per person
5 Jan - 11 Jan
found 1 hour ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$5,188, price is now AU$4,677 per person
AU$4,677
per person
5 Jan - 11 Jan
found 1 hour ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,938, price is now AU$4,481 per person
AU$4,481
per person
5 Jan - 11 Jan
found 1 hour ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Great stay near the riverwalk. Palms is great restaurant as well!

Reviewed on 31 Oct 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was AU$4,858, price is now AU$4,470 per person
AU$4,470
per person
5 Jan - 11 Jan
found 1 hour ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
We stayed here for 3 nights and enjoyed it would stay here again! Very simple hotel nothing extra no pool. Perfect to explore the city close to attractions

Reviewed on 31 Oct 2026

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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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

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$201 per night from 23 Nov to 24 Nov
AU$201
23 Nov - 24 Nov
includes taxes & fees
8.6/10 Excellent! (2,183 reviews)
"Great trip"

Reviewed on 1 Nov 2026

The Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 11 Nov to 12 Nov
AU$190
11 Nov - 12 Nov
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
162 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 22 Nov to 23 Nov
AU$175
22 Nov - 23 Nov
includes taxes & fees
8.6/10 Excellent! (2,360 reviews)
"Good stay, has the basics for sleeping after a night out. Small but adequate"

Reviewed on 31 Oct 2026

Hotel Saint Clair- Magnificent Mile
See all 4,603 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
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Streeterville holiday package cost?
Maybe less than you might think — from as low as AU$4,460, 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.

Stay near popular Streeterville attractions

A city intersection with tall buildings, including a historic building labeled "Water Tower Place."

Water Tower Place

9.0/10 (1,113 reviews)
Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.
See properties

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.