Old Town Chicago Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Aug 13 - Aug 18

    The Westin Chicago Lombard + Flight

    Lombard
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,260 reviews)
    "Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has gone down hill for sure"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,314
    NZ$2,826
    per traveller
    found 1 day ago
    The Westin Chicago Lombard
  • 55-inch TV with cable channels, video game console, pay films
    Aug 12 - Aug 17

    Hilton Chicago O'Hare Airport + Flight

    O'Hare
    5 nights
    4.0 star property
    8.4/10 - Very good (2,304 reviews)
    "It was a clean room but in AM ready to go in bathroom and who comes out of the bathroom was a large brown cockroach! Yikes!"
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,056
    NZ$3,237
    per traveller
    found 1 day ago
    Hilton Chicago O'Hare Airport
  • Coffee shop
    Aug 12 - Aug 17

    Hilton Rosemont Chicago O'Hare + Flight

    Rosemont
    5 nights
    3.5 star property
    8.4/10 - Very good (1,000 reviews)
    "Great"
    Reviewed May 25, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,302
    NZ$3,509
    per traveller
    found 1 day ago
    Hilton Rosemont Chicago O'Hare
  • Bar (on property)
    Aug 12 - Aug 17

    Embassy Suites by Hilton Chicago O'Hare Rosemont + Flight

    Rosemont
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,397 reviews)
    "Very nice interior in this hotel and I loved my 1 bedroom big unit. There is nice breakfast available and social hour, however bartender was rude. Bathtub was not perfectly clean. No shower handle, only shower head. Overall hotel a little dates but the beds were very comfortable"
    Reviewed May 30, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,674
    NZ$3,097
    per traveller
    found 1 day ago
    Embassy Suites by Hilton Chicago O'Hare Rosemont
  • Exterior
    Aug 12 - Aug 17

    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG + Flight

    Des Plaines
    5 nights
    3.0 star property
    8.8/10 - Excellent (1,855 reviews)
    "Clean and comfortable."
    Reviewed May 30, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,349
    NZ$2,834
    per traveller
    found 1 day ago
    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Our guide on where to stay in Old Town Chicago

Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
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

Our pick of the best Old Town Chicago 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 NZ$258 per night from 29 June to 30 June
NZ$258
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"

Reviewed on 29 May 2026

Congress Plaza Hotel
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 NZ$423 per night from 30 June to 1 July
NZ$423
30 June - 1 July
includes taxes & fees
9.4/10 Exceptional! (4,288 reviews)
"Staff was super nice and attentive."

Reviewed on 29 May 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 refundable
The price is NZ$302 per night from 29 June to 30 June
NZ$302
29 June - 30 June
includes taxes & fees
7.8/10 Good! (1,488 reviews)
"rooftop"

Reviewed on 29 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,634 properties in Old Town Chicago
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.

Frequently asked questions

How much does an Old Town Chicago holiday package cost?
Maybe less than you might think — from just , in fact! By bundling flights, hotels and car rentals into a tailor-made package, your Old Town Chicago escape is just a few clicks away.
How do I get a cheap travel package to Old Town Chicago?
Just think of all the fun things you could do in Old Town Chicago with a wad of extra cash in your pocket. Watch your savings stack up when you bundle your flights, hotels and extras into an Old Town Chicago holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can pick from more than 550 airlines and 1 000 000 properties worldwide. Whether you're heading away with the whole family or surprising your special someone, organising a getaway to Old Town Chicago is better with a package.
Where should I stay in Old Town Chicago?
Take the hassle out of sightseeing by staying someplace close to Old Town Chicago's iconic attractions. Wrigley Field and Lincoln Park Zoo are two of the most popular.
What are the top hotels in Old Town Chicago?
The Sono Chicago and Hotel Lincoln, part of JdV by Hyatt are among the most well-known properties in Old Town Chicago. Why not look up the rates and facilities at each and then decide?
How far in advance should I book my Old Town Chicago holiday?
While prices change frequently, we generally recommend booking your holiday as soon as possible. Most international airfares are available on Expedia up to a year in advance. If circumstances have left you booking late, you might still be in luck. Cheap journeys to Old Town Chicago sometimes emerge only weeks before departure.
What does an Expedia Old Town Chicago travel package include?
Hotels, flights and rental cars, or any combination of the three — you decide! Whether you're exploring Old Town Chicago with the kids or adventuring solo, there's a package to fit every style and budget. Once you've made your booking, why not add on a couple of tours and experiences?
What should I know before booking an Old Town Chicago travel package?
You'll score impressive savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything in one spot just makes things easier. So why waste your money or time? Whether you're putting together a luxury city stay with your love or a budget solo adventure, browse our holiday packages today.
Can I choose my airline with an Old Town Chicago Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're eager to fly to Old Town Chicago in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Old Town Chicago holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.