Rush Street Vacation Packages

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Top Rush Street Vacation Deals

Price found within the past 48 hours. Click for updated prices.
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 CA $1,545, price is now CA $1,111 per person
CA $1,111
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Beautiful place and at a breath taking spot. Staff in the front were very helpful. Good, clean and the most important thing is that its private for the guests. There is a security at the entrance of the pier so nobody can come in. Guests can take walks at the pier, but not the whole pier but some areas. Security was very helpful and understanding. 2 things that need work are: 1. Pillows: the pillows were a pain in the neck. 2. The body wash: our room had an empty bottle of body wash and wasn't replaced for 2 days. Thank goodness, we had our own. And the bodywash holder was broken as well. maybe that is the case. Other then that, i would stay here every chance I get and would recommend it to everyone. Thank you to all the hotel staff for making our visit so memorable. Thank you Sable for the beautiful views, right from our room and thank you Chicago.

Reviewed on May 31, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,744, price is now CA $1,158 per person
CA $1,158
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Staff was so helpful

Reviewed on May 29, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,919, price is now CA $1,301 per person
CA $1,301
per person
Aug 11 - Aug 15
found 2 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,017 reviews)
Great room with excellent views!

Reviewed on May 30, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,769, price is now CA $1,239 per person
CA $1,239
per person
Jul 6 - Jul 10
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (395 reviews)
Great location and well maintained property!

Reviewed on May 29, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,795, price is now CA $1,285 per person
CA $1,285
per person
Aug 21 - Aug 24
found 6 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
Would definitely stay here again! Clean, friendly staff, great location.

Reviewed on May 23, 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 $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on May 31, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 14 to Jun 15
CA $210
CA $249 total
Jun 14 - Jun 15
includes taxes & fees
7.8/10 Good! (1,497 reviews)
"Everything was great"

Reviewed on May 31, 2026

The Chicago Hotel Collection - Magnificent Mile
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 $261 per night from Jun 30 to Jul 1
CA $261
CA $349 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,306 reviews)
"This hotel is absolutely lovely! Immaculate in every area, with very helpful and friendly staff. The room was perfectly appointed. The bathroom door doubled as a door to the toilet and I want one of those in my house! The rain shower with a wand had great water pressure and temperature. I'm not a ..."

Reviewed on May 31, 2026

Hotel Riu Plaza Chicago
See all 4,588 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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Discover the most popular places to visit in Rush Street

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Rush Street

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 Rush Street

Frequently asked questions

Can I cancel my flight booking to Rush Street due to COVID-19?
Our convenient Customer Service Portal is your one-stop shop for most travel questions, including about flight changes and cancellations due to COVID-19. For greater peace of mind, look over the terms and conditions of your airfare before booking your next flight.
What's the best way to find cheap flights to Rush Street that have flexible change policies?
When it comes to traveling these days, flexibility is important. That's why we've added a "No change fee" filter to help you locate flexible, low-priced fares to Rush Street. It's near the top left of your screen directly under the "Flexible change policies" heading.
What are some of the general tips for travelers to Rush Street during the COVID-19 outbreak?
COVID-19 has transformed how the world works in countless ways, including how we're able to travel safely. These tips will help you navigate the new challenges and get you ready for your trip to Rush Street:
  • Investigate what, if any, restrictions or rules apply to both your origin and destination. You may not be able to travel depending on local circumstances, so make sure you check before you lock in your flight.
  • When you pass through airport checkpoints, keep your face mask on. You will be asked to lower it briefly to verify your identity. Passengers who refuse to wear a mask may face civil penalties and may also be denied boarding.
  • You're no longer required to hand your boarding pass (paper or electronic) directly to a TSA employee. Instead, you should position the pass on the reader and then hold it up for the agent to visually inspect it.
  • One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must be no bigger than 12 oz (350 ml), and you'll have to take it out of your bag at the X-ray machine for scanning.
  • To minimize handling during the screening process, put items such as your belt, phone and wallet into your carry-on rather than into the bins.
  • Separate any food you're carrying for X-ray scanning. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to handle and inspect your belongings.

Which airlines fly to Rush Street?
American Airlines is a well-known air carrier servicing Rush Street. Search for a ticket to O'Hare Intl. Airport (ORD) and you'll have 13307 American Airlines flights every month to pick from.
How can I find cheap tickets to Rush Street?
You'll always score an awesome deal with Expedia, but our "flexible dates" feature makes it even easier. Enter your preferred flight date, then check the flexible dates box above to compare prices for nearby days. was the lowest price for a flight to Rush Street in the last seven days.
How much is a flight to Rush Street?
The cost of a round-trip airfare to Rush Street in the last seven days ranged between and . If you were journeying one way out of (), you could have landed a fare from just .
What are the most popular airports to fly into in Rush Street?
The principal gateway to Rush Street, around 33491 flights cruise into O'Hare Intl. Airport (ORD) each month. Track down an unbeatable deal, book your ticket and get set to explore this fantastic region.
When is the cheapest time to fly to Rush Street?
Consider leaving early on in the week to land a bargain airfare to Rush Street. Tuesday is normally the most economical day to fly, followed by Monday. Saturday typically has the highest ticket prices. This is because a lot of travelers prefer to begin their vacation on a weekend.
How much is a plane ticket to Rush Street?
Ticket prices to Rush Street varied from to in the last seven days. Normally, the sooner you book the better the deal.
Which airlines with flights to Rush Street employ COVID-19 cleanliness policies?
As people take to the skies once again, most reputable airlines have introduced physical distancing and other preventive measures to help slow the spread of COVID-19. Here are some of them:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.