Streeterville Trips (flight + hotel)

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Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
Downtown Chicago which includes 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 P8,202 per night from Aug 24 to Aug 25
P8,202
P9,628 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,599 reviews)
"The staff was helpful and kind, the room was clean but did have a constant running toilet. The view from the room was amazing. The area was walkable to everywhere I wanted to go. There was a great place to eat right at the hotel that had an amazing breakfast. All in all it was a good stay."

Reviewed on Aug 9, 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 P8,621 per night from Sep 1 to Sep 2
P8,621
P10,121 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,164 reviews)
"Our pocket door for the bathroom did not have a handle so it was hard to open and close"

Reviewed on Aug 10, 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 P7,071 per night from Sep 2 to Sep 3
P7,071
P8,300 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (3,522 reviews)
"Breakfasts were good. Beds were comfortable."

Reviewed on Aug 10, 2025

The Whitehall Hotel, BW Premier Collection
See all 4,652 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 vacation 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 vacation 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 vacation 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 vacation 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 neighborhood's most in-demand hotels. Another well-known option in Streeterville is Omni Chicago Hotel.
How far in advance should I book my Streeterville vacation?
Travelers 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 vacation rentals such as mountain cabins and spacious residences. The list goes on!
Can I choose my airline with a Streeterville Expedia vacation 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 vacation.
If I'm not able to travel, can I cancel my Streeterville vacation package?
Yes you can, and we're here to help. You may be able to cancel or amend your Streeterville vacation 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

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

Harry Potter Shop Chicago

You can browse for the perfect souvenirs at Harry Potter Shop Chicago during your visit to Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Harry Potter Shop Chicago

Things to do

River tour boat in Chicago

Architecture River Tour

P2,350
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

P2,551
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

P1,698
per adult
92% of travellers recommend
Skyline Lake 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.