Far Southwest Side Holidays from NZ$2,216

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

The Latest Far Southwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$2,620, price is now NZ$2,216 per person
NZ$2,216
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on 10 Nov 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was NZ$2,690, price is now NZ$2,263 per person
NZ$2,263
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
Great location, friendly staff, lovely rooms!

Reviewed on 10 Nov 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was NZ$3,882, price is now NZ$3,296 per person
NZ$3,296
per person
21 Dec - 26 Dec
found 23 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,141 reviews)
It's an old airport hotel. What does one should expect, 5 stars?? Served the purpose. Didn't eat food only slept for one night due to the flight cancelation.

Reviewed on 10 Nov 2025

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Price was NZ$2,774, price is now NZ$2,360 per person
NZ$2,360
per person
22 Dec - 27 Dec
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,013 reviews)
The room itself was clean and had a great view.

Reviewed on 10 Nov 2025

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,357, price is now NZ$3,743 per person
NZ$3,743
per person
21 Dec - 26 Dec
found 23 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
It was very nice. Staff was great

Reviewed on 10 Nov 2025

Our guide on where to stay in Far Southwest Side

Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
Default Image

Beverly

Beverly is well liked for its restaurants and churches. If you're hoping to see more of the larger area, Martin Luther King Drive and Harborside International Golf Center are some interesting sights nearby to check out.

Find hotels in Beverly

Far Southwest Side Holiday

Our pick of the best Far Southwest Side Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$222 per night from 24 Nov to 25 Nov
NZ$222
24 Nov - 25 Nov
includes taxes & fees
8.4/10 Very Good! (5,199 reviews)
It was fine

Reviewed on 5 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
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$211 per night from 7 Dec to 8 Dec
NZ$211
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,243 reviews)
Large, clean spacious rooms. Convenient to shopping and restaurants. A very good bargain for the price.

Reviewed on 8 Nov 2025

Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,538 reviews)
a

Reviewed on 8 Nov 2025

Get rates
Congress Plaza Hotel
See all 4,756 properties in Far Southwest Side
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 Far Southwest Side

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

Wrigley Field

4.5/5(21 reviews)

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

4.5/5(21 reviews)

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
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Millennium Park

What to do in Far Southwest Side

River tour boat in Chicago

Architecture River Tour

NZ$85
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

NZ$76
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Far Southwest Side

Frequently asked questions

Can I cancel my flight booking to Far Southwest Side due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already reserved your flight to Far Southwest Side, make use of our Customer Service Portal. It will help determine which COVID-19 policies are applicable to your reservation and provide you with the next steps.
What's the best way to find cheap flights to Far Southwest Side that have flexible change policies?
When it comes to travelling these days, flexibility is crucial. That's why we've added a "No change fee" filter to help you locate cheap and flexible tickets to Far Southwest Side. 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 Far Southwest Side during the COVID-19 outbreak?
COVID-19 has ushered in dramatic changes to how we travel. If you're planning an escape to Far Southwest Side, these tips will help you navigate these new rules and challenges:
  • Before you lock in a flight, check if any travel restrictions apply — in both your origin and destination. Stay informed with the latest updates by reviewing government travel advisories.
  • When you go through airport screening, keep your face mask on. You will be required to lower it briefly to verify your identity. Passengers who refuse to wear a mask may be fined and denied boarding.
  • Rather than handing a TSA agent your boarding pass, position it directly on the reader yourself. After that, hold it up for inspection.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will have to be removed from your bag for scanning.
  • Place any personal items (e.g, keys, phone and wallet) in your carry-on rather than a bin to reduce handling during the screening process.
  • Separate any food you have for X-ray screening. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to handle and inspect your belongings.

Which airlines fly to Far Southwest Side?
Organise your seat with American Airlines and then start putting together your Far Southwest Side travel itinerary. This leading carrier provides 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Far Southwest Side?
In the last seven days, was the lowest price for a flight to Far Southwest Side. For an even cheaper fare, book well ahead of time and be flexible with your dates. Search for your trip to Far Southwest Side, then compare prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Far Southwest Side?
In the last seven days, round-trip airfares to Far Southwest Side sold from just and reached a maximum price of . For one-way fares taking off from (), the cheapest seat during this time was only .
What are the most popular airports to fly into in Far Southwest Side?
Start arranging your Far Southwest Side holiday by booking a fare on one of the 33491 flights each month to O'Hare Intl. Airport (ORD). This is the region's main entry point.
When is the cheapest time to fly to Far Southwest Side?
If you'd prefer to spend your holiday money enjoying the best of Far Southwest Side rather than on your flight there, jet off earlier in the week. The most affordable day to travel is normally Tuesday, with Monday a close second. With many folks travelling over the weekend, Saturday often has the highest ticket prices.
How much is a plane ticket to Far Southwest Side?
Fares to Far Southwest Side varied from to in the last seven days. Typically, the quicker you book the better the price.
Which airlines with flights to Far Southwest Side employ COVID-19 cleanliness policies?
As countries begin to open their borders, most airlines have resumed business with new measures including physical distancing and enhanced disinfection measures. Here's what different carriers are doing to ease the spread of COVID-19:
  • 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.

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