Drexel Estate 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 (1,255 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 20 hours 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 (2,303 reviews)
    "No complaints"
    Reviewed May 28, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$4,056
    NZ$3,237
    per traveller
    found 20 hours 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 20 hours 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 (1,394 reviews)
    "CAR"
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,674
    NZ$3,097
    per traveller
    found 20 hours 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 (1,853 reviews)
    "Very friendly staff, room was super clean and lots of nearby restaurants and 5 minutes from airport. Great location!"
    Reviewed May 29, 2026
    Return • Auckland (AKL) - Chicago (ORD)
    AKL - ORD • 2 stops ORD - AKL • 2 stops
    NZ$3,349
    NZ$2,834
    per traveller
    found 20 hours ago
    Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Our guide on where to stay in Drexel Estate

Find the best Drexel Estate areas and neighborhoods for the activities you enjoy most. Learn more about Drexel Estate
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 Drexel Estate 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$261 per night from 29 June to 30 June
NZ$261
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$479 per night from 29 June to 30 June
NZ$479
29 June - 30 June
includes taxes & fees
9.4/10 Exceptional! (4,287 reviews)
"Nice place"

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$304 per night from 28 June to 29 June
NZ$304
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,487 reviews)
"rooftop"

Reviewed on 29 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,716 properties in Drexel Estate
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 a Drexel Estate holiday package cost?
Perhaps less than you might think — from just , as a matter of fact! By combining hotels, flights and car rentals into a custom-built holiday package, your trip to Drexel Estate is just clicks away.
How do I get a cheap travel package to Drexel Estate?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Pick a combination that suits you and watch your savings pile up. Of course, a travel package is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1 000 000 properties across the world, which lets you customize your Drexel Estate holiday.
Where should I stay in Drexel Estate?
We recommend staying near the action. Many travellers like to book hotels in the vicinity of top attractions, like Marquette Park, St. Bernard Hospital and Balzekas Museum of Lithuanian Culture.
How far in advance should I book my Drexel Estate holiday?
Reward yourself with the widest variety and the lowest prices by booking your Drexel Estate adventure early. Air carriers tend to publish tickets anywhere up to a year prior to departure, so start locking things in ASAP. Having said that, Expedia is constantly working to give you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Drexel Estate travel package include?
Expedia has everything you need to book your Drexel Estate trip, but how you structure your package is up to you. Pick from any combination of hotels, flights and rental cars. Searching for some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. Whatever your budget, there's a package deal to meet your needs.
What should I know before booking a Drexel Estate travel package?
A travel package can be customized for your budget and is a great way to make your budget go further. What you include is completely up to you. Hotels, rental cars and flights — decide on a combination that suits your plans.
Can I choose my airline with a Drexel Estate Expedia holiday package?
Yes, the choice is yours. We offer more than 550 partner airlines all over the world, so you can tailor your Drexel Estate adventure according to your budget and travel needs.
If I'm not able to travel, can I cancel my Drexel Estate holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. To learn more, visit our Customer Service Portal. But generally speaking, if you've booked your Drexel Estate holiday package in the last 24 hours, you may be able to change or cancel it without penalty. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Drexel Estate

Wrigley Field

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
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
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

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.