Streeterville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Executive lounge
    Jul 28 - Jul 31

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    8.8/10 - Excellent (2,164 reviews)
    "Amazing staff. Clean rooms!"
    Reviewed May 21, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,344
    CA $940
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park
  • Indoor wedding
    Jul 28 - Jul 31

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,336 reviews)
    "Great location and very convenient to river walk and vicinity."
    Reviewed May 22, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,579
    CA $1,040
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Lounge
    Jul 28 - Jul 31

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,116 reviews)
    "Great staff and perfect place to be in the middle of everything!"
    Reviewed April 27, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,707
    CA $1,146
    per traveller
    found 1 day ago
    Pendry Chicago
  • View from property
    Jun 27 - Jul 1

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (116 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YKF • Nonstop
    CA $1,574
    CA $1,063
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Terrace/patio
    Jul 28 - Jul 31

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,506 reviews)
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,502
    CA $1,042
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton

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

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

Streeterville Hotel Deals

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 CA $220 per night from May 27 to May 28
CA $220
CA $301 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,214 reviews)
"One of the best hotels I’ve stayed in!"

Reviewed on May 23, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from May 25 to May 26
CA $168
CA $199 total
May 25 - May 26
includes taxes & fees
The Chicago Hotel Collection - Magnificent Mile
Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
The price is CA $206 per night from May 26 to May 27
CA $206
CA $245 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (3,239 reviews)
"Valet parking was easy and worth the extra money to be able to take your car in and out of it a few times during your stay. Hotel room had great views on the 18th floor with tall ceilings. Room was clean and had everything I needed and lots of space. The bathroom barn door style was sticking at one ..."

Reviewed on May 20, 2026

Aloft by Marriott Chicago Mag Mile
See all 4,633 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.

Discover the most popular places to visit in Streeterville

Water Tower Place

Water Tower Place

4.5/5(67 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(194 reviews)

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

875 North Michigan Avenue
900 North Michigan Shops

900 North Michigan Shops

4/5(5 reviews)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

900 North Michigan Shops

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
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.