Streeterville Holidays from £729
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Your Streeterville Holiday
If you're wanting a lakeside escape, our Streeterville holiday packages are what you need. Whether you want to experience its families, history or culture, this neighbourhood has a little bit of something for everyone. Some leading nearby attractions to see during your trip to Streeterville include Millennium Park, Willis Tower and Art Institute of Chicago. Stop dreaming and start doing. When you're ready to book your holiday to Streeterville, Expedia is here to help.
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
£729
per person
7 Nov - 12 Nov
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on 19 Aug 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
£1,159
per person
7 Nov - 12 Nov
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Amazing hotel. We go every year and always have a great time.
We were greeted with a warm hand towel and champagne.
Reviewed on 19 Aug 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
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Streeterville
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
£113
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (1,984 reviews)
"Came in on a Sunday and met the wonderful and incredibly helpful Raymond. He was super friendly and accommodating. The hotel had erroneously taken a $330 payment from my credit card that i had on file even though I had prepaid in full, and while it was set to refund back to my card it still left ..."
Reviewed on 19 Aug 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
£177
31 Aug - 1 Sept
includes taxes & fees
The Wade
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
£148
23 Aug - 24 Aug
includes taxes & fees
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 travel package cost?
From as little as £729. Yes, you read that correctly. Our Streeterville packages are the quickest way to stretch your budget further. Combine your preferred flights, hotels and rental car and discover this popular destination.
If I'm not able to travel, can I cancel my Streeterville travel package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Locked in your Streeterville travel package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may be charged a fee by your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Streeterville?
Booking a Streeterville travel package with Expedia is such a simple way to save. We offer access to over 550 partner airlines and 1,000,000 hotel options spread across the globe. With such a fabulous range to pick from, you'll have no difficulty putting together your next dream getaway.
Does Expedia offer Book Now, Pay Later Streeterville holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:
- Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
- Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
- Low deposit holidays: When you stumble on an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.
Where should I stay in Streeterville?
Visitors come from all over the world to experience Millennium Park and Wrigley Field in Streeterville. Stay close to these fantastic attractions and visit them whenever you want.
What are the top hotels in Streeterville?
Make a reservation at Hyatt Regency Chicago. It's one of this area's most sought-after hotels. Another highly rated option in Streeterville is The Godfrey Hotel Chicago.
How far in advance should I book my Streeterville holiday?
It's difficult to pick the ideal time for airfares, but we generally say the earlier, the better. Most international journeys on Expedia become available up to 12 months in advance. If you can't book early, fear not. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Streeterville travel package include?
Much of that depends on you. You can pick from a range of Streeterville bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your ideal Streeterville trip looks like, get ready to save!
What should I know before booking a Streeterville travel package?
When you book your flights, hotels and car rentals together, you'll land great discounts. Whether you're planning a beach break in a villa or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Streeterville Expedia travel package?
You can. Expedia has access to more than 550 partner airlines around the world, so fly with the carrier that matches your needs.
Stay near popular Streeterville attractions
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.
875 North Michigan Avenue
9.2/10 (2,926 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 fascinating museums.
Photo by daniel jersey
Chicago Children's Museum
9.2/10 (237 reviews)
You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Tribune Tower
8.6/10 (76 reviews)
You can learn about the history of Chicago with a visit to Tribune Tower. Discover the fascinating museums and notable monuments in this vibrant area.
Photo by Rita Irvine
900 North Michigan Shops
8.6/10 (55 reviews)
You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
Museum of Contemporary Art Chicago
9.0/10 (88 reviews)
You can spend an afternoon studying the exhibits at Museum of Contemporary Art Chicago during your trip to Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
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 fascinating museums.
Broadway Playhouse
8.4/10 (17 reviews)
You can make plans for a show at Broadway Playhouse during your stay in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.