Downtown Skokie Holidays
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- The Westin Chicago Lombard
Aug 13 - Aug 18The Westin Chicago Lombard + Flight
Lombard5 nights9.0/10 - Wonderful (1,254 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, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$3,314NZ$2,826found 16 hours agoper traveller - Hilton Chicago O'Hare Airport
Aug 12 - Aug 17Hilton Chicago O'Hare Airport + Flight
O'Hare5 nights8.4/10 - Very good (2,303 reviews)"No complaints"Reviewed May 28, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$4,056NZ$3,237found 16 hours agoper traveller - Hilton Rosemont Chicago O'Hare
Aug 12 - Aug 17Hilton Rosemont Chicago O'Hare + Flight
Rosemont5 nights8.4/10 - Very good (1,000 reviews)"Great"Reviewed May 25, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$4,302NZ$3,509found 16 hours agoper traveller - Embassy Suites by Hilton Chicago O'Hare Rosemont
Aug 12 - Aug 17Embassy Suites by Hilton Chicago O'Hare Rosemont + Flight
Rosemont5 nights8.8/10 - Excellent (1,392 reviews)"Good!"Reviewed May 26, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$3,674NZ$3,097found 16 hours agoper traveller - Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
Aug 12 - Aug 17Holiday Inn Express & Suites Chicago O'Hare Airport by IHG + Flight
Des Plaines5 nights8.8/10 - Excellent (1,851 reviews)"Stayed one night, quiet and close to the airport. Food and gas station convenient. Great location for an early flight."Reviewed May 28, 2026Return • Auckland (AKL) - Chicago (ORD)AKL - ORD • 2 stops ORD - AKL • 2 stopsNZ$3,349NZ$2,834found 16 hours agoper traveller
Our guide on where to stay in Downtown Skokie
Find the best Downtown Skokie areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Skokie
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.
Our pick of the best Downtown Skokie Hotel Deals
Congress Plaza Hotel
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! (10,121 reviews)
"The Congress is old but it never fails!!! Great location!!! I have stayed there many of times …"
Reviewed on 28 May 2026
Hotel Riu Plaza Chicago
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! (4,286 reviews)
"Amazing breakfasts"
Reviewed on 29 May 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is NZ$304 per night from 29 June to 30 June
NZ$304
29 June - 30 June
includes taxes & fees
7.8/10 Good! (1,486 reviews)
"The hotel was amazing looked exactly like the photos. The staff was awesome 10/10 I would for sure stay here again!"
Reviewed on 29 May 2026
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 Downtown Skokie
Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.
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.
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.
Activities
Skydeck - Willis Tower Admission
NZ$74
per adult
96% of travellers recommend
Chicago Sightseeing River and Lake Cruise
NZ$77
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.