Rush Street Holidays from NZ$2,395

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The Latest Rush Street Holiday 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 NZ$2,901, price is now NZ$2,395 per person
NZ$2,395
per person
21 Jan - 26 Jan
found 7 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
The room was immaculate. We were very happy.

Reviewed on 18 Dec 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,972, price is now NZ$3,868 per person
NZ$3,868
per person
21 Jan - 26 Jan
found 7 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!

Reviewed on 19 Dec 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,112, price is now NZ$2,499 per person
NZ$2,499
per person
21 Jan - 26 Jan
found 7 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Overall good experience. My room was not cleaned one of the nights because the maid didn’t come until late but we were already in our room. Also, the $25/night resort fee was not properly explained to me, didn’t make much sense at all honestly. Property is nice and in a great location but i wouldn’t stay here again

Reviewed on 19 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,198, price is now NZ$2,579 per person
NZ$2,579
per person
21 Jan - 26 Jan
found 7 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was NZ$3,037, price is now NZ$2,511 per person
NZ$2,511
per person
21 Jan - 26 Jan
found 7 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again

Reviewed on 20 Dec 2025

Rush Street Holiday

Our pick of the best Rush Street Hotel Deals

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 NZ$182 per night from 5 Jan to 6 Jan
NZ$182
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,507 reviews)
Clean Room

Reviewed on 18 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,130 reviews)
Clean room, attentive staff, great lounge!

Reviewed on 15 Dec 2025

Get rates
Silversmith Hotel Chicago Downtown
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$301 per night from 26 Dec to 27 Dec
NZ$301
26 Dec - 27 Dec
includes taxes & fees
8.4/10 Very Good! (2,134 reviews)
Clean room. I didn’t mind the old door knobs I liked it. Smaller room than anticipated but it was nice and clean.

Reviewed on 14 Dec 2025

Palmer House a Hilton Hotel
See all 4,672 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.

Discover the most popular places to visit in Rush Street

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

What to do in Rush Street

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$76
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of 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 travelling 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 travellers 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 travellers prefer to begin their holiday 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.