Streeterville Holidays

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    Save up to €900 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,174, price is now €955 per person
€955
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on 5 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,797, price is now €1,400 per person
€1,400
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything

Reviewed on 8 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €1,461, price is now €1,156 per person
€1,156
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on 8 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was €1,220, price is now €988 per person
€988
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on 6 May 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,158, price is now €966 per person
€966
per person
16 Jul - 19 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
If you’re up for walking, this hotel is a great place to stay close enough to most things.

Reviewed on 8 May 2026

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
Downtown Chicago

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

Top hotels in Streeterville

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €174 per night from 25 May to 26 May
€174
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,093 reviews)
The room was exceptionally clean and the staff was great! The location 1/2 block from Michigan Ave. We had a wonderful stay!

Reviewed on 9 May 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is €151 per night from 25 May to 26 May
€151
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,279 reviews)
Nice convenient location and lots of space to spread out

Reviewed on 8 May 2026

Hilton Chicago/Magnificent Mile Suites
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Fully refundableReserve now, pay when you stay
The price is €233 per night from 19 May to 20 May
€233
19 May - 20 May
includes taxes & fees
8.6/10 Excellent! (2,460 reviews)
Was ok. Breakfast wasn't stellar.

Reviewed on 8 May 2026

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
See all 4,615 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 €955, 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(25 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
875 North Michigan Avenue

875 North Michigan Avenue

4.5/5(85 reviews)

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

875 North Michigan Avenue
Chicago River During Christmas

Wrigley Building

4.5/5(3 reviews)

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

Wrigley Building

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.