Streeterville Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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

Top hotels in Streeterville

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 ฿4,657 per night from 17 Aug to 18 Aug
฿4,657
฿5,467 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,548 reviews)
"Great area, clean hotel but, parking is expensive. There was no pool."

Reviewed on 27 Jul 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 ฿3,876 per night from 24 Aug to 25 Aug
฿3,876
฿4,550 total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (3,543 reviews)
"Staff were nice to upgrade us because of my wife birthday coming up."

Reviewed on 27 Jul 2025

The Whitehall Hotel, BW Premier Collection
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 ฿4,344 per night from 17 Aug to 18 Aug
฿4,344
฿5,100 total
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,145 reviews)
"Very"

Reviewed on 28 Jul 2025

The Wade
See all 4,559 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 , 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 rentals 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.

Popular places to visit

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 fascinating museums.

John Hancock Center
Milton Lee Olive Park

Milton Lee Olive Park

Explore the great outdoors at Milton Lee Olive Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Milton Lee Olive Park

Things to do

River tour boat in Chicago

Architecture River Tour

฿1,345
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

฿1,314
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Architecture Boat Tour with Drinks

Chicago: Architecture Boat Tour with Drinks

฿1,363
per adult
86% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
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.