Streeterville Holidays

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Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,443, price is now €873 per person
€873
per person
4 Oct - 10 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,794, price is now €1,081 per person
€1,081
per person
4 Oct - 10 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €2,271, price is now €1,396 per person
€1,396
per person
2 Nov - 7 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €1,722, price is now €1,066 per person
€1,066
per person
4 Oct - 10 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on 25 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,713, price is now €1,117 per person
€1,117
per person
4 Oct - 10 Oct
found 9 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on 21 Aug 2025

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

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 €153 per night from 1 Sept to 2 Sept
€153
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,213 reviews)
Great hotel and location!
"Everything about the stay was awesome. The service, the guys handling the bags, the rooms, the custodians, the view from the balacony and gym. Especially the speed bag in the gym! I highly recommend this hotel, it was great to see the fireworks at Navy pier from the balacony as well."

Reviewed on 23 Aug 2025

The Wade
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 €162 per night from 1 Sept to 2 Sept
€162
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (2,684 reviews)
"Great area"

Reviewed on 23 Aug 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 €114 per night from 2 Sept to 3 Sept
€114
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (3,534 reviews)
"Close vicinity to all downtown attractions"

Reviewed on 22 Aug 2025

The Whitehall Hotel, BW Premier Collection
See all 4,587 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 €873, 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

4/5(24 reviews)

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

4.5/5(84 reviews)

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
The Loop - Downtown

Wrigley Building

4.5/5(3 reviews)

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Wrigley Building

Things to do

River tour boat in Chicago

Architecture River Tour

€36
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

€35
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

€36
per adult
88% 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.