Uptown Holidays
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- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
- Thompson Chicago, by Hyatt
Jul 28 - Aug 4Thompson Chicago, by Hyatt + Flight
Downtown Chicago7 nights9.2/10 - Wonderful (1,370 reviews)"Excellent hotel and close to restaurants and shopping. Very clean."Reviewed May 24, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$4,948AU$3,786found 1 day agoper traveller - Swissotel - Chicago
Jul 28 - Aug 4Swissotel - Chicago + Flight
Downtown Chicago7 nights9.0/10 - Wonderful (3,352 reviews)"They were extremely accommodating! Highly recommend."Reviewed May 26, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 28 - Aug 4Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago7 nights9.4/10 - Exceptional (2,516 reviews)"Clean and have a beautiful view of the lake"Reviewed May 26, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$5,762AU$4,025found 1 day agoper traveller - LondonHouse Chicago, Curio Collection by Hilton
Jul 28 - Aug 4LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago7 nights9.4/10 - Exceptional (3,727 reviews)"Excellent location! Great views from our room."Reviewed May 25, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$6,045AU$4,257found 1 day agoper traveller - Fairmont Chicago at Millennium Park
Jul 28 - Aug 4Fairmont Chicago at Millennium Park + Flight
Downtown Chicago7 nights8.8/10 - Excellent (2,171 reviews)"Amazing view and clean room"Reviewed May 25, 2026Return • Sydney (SYD) - Chicago (ORD)SYD - ORD • 1 stop ORD - SYD • 1 stopAU$5,126AU$3,886found 1 day agoper traveller
Our pick of the best Uptown Hotel Deals
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 17 June to 18 June
AU$237
17 June - 18 June
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Clean room. Extremely friendly and helpful staff. Very family friendly. Overall a great experience."
Reviewed on 23 May 2026
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 7 June to 8 June
AU$121
7 June - 8 June
includes taxes & fees
8.2/10 Very Good! (166 reviews)
"No elevators, no towels, small rooms"
Reviewed on 24 May 2026
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 27 May to 28 May
AU$164
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Perfect for our stay of less than 12 hours. Great breakfast! At check-in, they offered us a carpeted room or a non-carpeted room. It was nice to have the choice. Clean, basic accommodations."
Reviewed on 26 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 Uptown
Dinosaur Discovery Museum
You can spend time browsing the exhibits at Dinosaur Discovery Museum in Kenosha. Wander the lakeside and beaches in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.