Rush Street Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Rush Street Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $984, price is now CA $740 per person
CA $740
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,050, price is now CA $776 per person
CA $776
per person
Dec 4 - Dec 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,154, price is now CA $879 per person
CA $879
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $981, price is now CA $759 per person
CA $759
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,877, price is now CA $1,456 per person
CA $1,456
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
The best of the best. The largest rooms in town at the very best price with the very best experience.

Reviewed on Oct 26, 2026

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Rush Street Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Nov 22 to Nov 23
CA $146
CA $174 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (10,118 reviews)
"The rooms were really small and it could use some updating for sure however it did have a vintage feel and really nice restaurant and bar with very nice staff. Parking was expensive and on a different block which was inconvenient"

Reviewed on Oct 27, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Nov 22 to Nov 23
CA $170
CA $203 total
Nov 22 - Nov 23
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 23 to Nov 24
CA $162
CA $193 total
Nov 23 - Nov 24
includes taxes & fees
8.8/10 Excellent! (5,575 reviews)
"Not the greatest property, outdated"

Reviewed on Oct 26, 2026

River Hotel
See all 4,607 properties in Rush Street
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.
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What to do in Rush Street

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $57
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Rush Street

Frequently asked questions

How much does a Rush Street vacation package cost?
Our Rush Street vacation packages, which start from as low as CA $740, are the perfect way to save loads of cash. Pick your favorite hotels, flights and more to create your perfect escape.
How do I get a cheap travel package to Rush Street?
Combine your bookings with Expedia to save big on your next adventure. With more than 550 air carriers and 1,000,000 properties globally, your Rush Street vacation package can be customized exactly to suit your travel style. With all that extra money, why not include one or two exciting activities and tours? It's an easy way to unlock even more savings. That dream vacation to Rush Street is much closer than you thought!
Where should I stay in Rush Street?
Travelers come from all over to experience McCormick Place and Millennium Park in Rush Street. Book a hotel close to these popular attractions and visit them at your leisure.
What are the top hotels in Rush Street?
Thompson Chicago, part of Hyatt is one of Rush Street's leading hotels. Reserve a room here and you can sleep soundly knowing you're in good hands.
How far in advance should I book my Rush Street vacation?
Search Expedia to compare international airfares as soon as you know your travel dates. You can normally purchase a seat up to a year before departure. If you don't see your preferred air carrier, or you have to book last minute, fear not. Cheap tickets to Rush Street sometimes appear just weeks before departure.
What does an Expedia Rush Street travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to build your perfect Rush Street travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Don't forget, the more you bundle, the more deals you'll score!
What should I know before booking a Rush Street travel package?
Bundling your bookings into a Rush Street vacation package is the easiest way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Rush Street Expedia vacation package?
Definitely. Expedia has more than 550 partner airlines to pick from worldwide. With so much choice, finding the ideal carrier to bring you to Rush Street won't be hard.
If I'm not able to travel, can I cancel my Rush Street vacation package?
Whether it's your hotel or flight, you can cancel and rebook it. Locked in your Rush Street vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. If it's been longer than that, you may be charged a fee by your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We'll help you every step of the way.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.