Streeterville Holidays from £1,900

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.
Best Western Plus O'Hare International South Hotel

Best Western Plus O'Hare International South Hotel

2.5 out of 5
Price was £3,295, price is now £1,900 per person
£1,900
per person
16 Aug - 20 Aug
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
7.4/10 Good! (1,003 reviews)
The room was cleaned as requested, close to the elevator—great Full breakfast. The staff was very helpful. Will stay here again. Driver of airport shuttle was very polite and helpful.

Reviewed on 3 Jul 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was £3,579, price is now £2,064 per person
£2,064
per person
16 Aug - 20 Aug
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,139 reviews)
Room was nice and spacious. I appreciated the breakfast and happy hour.

Reviewed on 4 Jul 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
Price was £3,343, price is now £1,940 per person
£1,940
per person
16 Aug - 20 Aug
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
7.6/10 Good! (1,547 reviews)
The pool was very dirty i didn't get a chance to use it. I had alot of bugs in my room from the rain i assume.

Reviewed on 4 Jul 2026

Motel 6 Schiller Park, IL - Chicago O'Hare

Motel 6 Schiller Park, IL - Chicago O'Hare

2 out of 5
Price was £3,289, price is now £1,910 per person
£1,910
per person
17 Aug - 22 Aug
found 5 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
6.8/10 (2,198 reviews)
Staff were warm and welcoming. The area wasn’t the greatest. Very loud at night and the room had a terrible smell.

Reviewed on 5 Jul 2026

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

3.5 out of 5
Price was £3,357, price is now £1,959 per person
£1,959
per person
17 Aug - 22 Aug
found 5 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
7.6/10 Good! (1,755 reviews)
Room was very clean and staff was great.

Reviewed on 4 Jul 2026

Where to stay in Streeterville

Find the best Streeterville areas and neighborhoods for the activities you enjoy most. Learn more about Streeterville
A busy city street with tall buildings, a bus, and cars.

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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £155 per night from 8 Jul to 9 Jul
£155
8 Jul - 9 Jul
includes taxes & fees
9.2/10 Wonderful! (1,846 reviews)
"Great staff"

Reviewed on 5 Jul 2026

Omni Chicago Hotel
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 £173 per night from 7 Jul to 8 Jul
£173
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (4,497 reviews)
"Hotel staff and room were Chicago nice! And it would seem they are some of the nicest people. We had a great stay."

Reviewed on 5 Jul 2026

Hilton Chicago/Magnificent Mile Suites
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 £216 per night from 19 Jul to 20 Jul
£216
19 Jul - 20 Jul
includes taxes & fees
9.4/10 Exceptional! (4,622 reviews)
"Excellent customer service, amazing staff!"

Reviewed on 4 Jul 2026

Hotel Riu Plaza Chicago
See all 4,379 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Streeterville travel package cost?
From as little as £1,900. 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

A castle-like structure with turrets and a modern skyscraper in the background.

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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.