Chicago Adventure Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top flight + Adventure hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Lincoln
Lincoln Park
Price was AU$1,914, price is now AU$1,739 per person
AU$1,739
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
7.8/10 Good! (1,094 reviews)
Staff was very friendly and helpful made my stay a lot more enjoyable
Reviewed on 25 Apr 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
Price was AU$3,151, price is now AU$2,251 per person
AU$2,251
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (3,002 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!
Reviewed on 24 Apr 2026
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$3,643, price is now AU$2,845 per person
AU$2,845
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.6/10 Excellent! (2,742 reviews)
Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.
Reviewed on 22 Apr 2026
5* Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was AU$3,731, price is now AU$3,647 per person
AU$3,647
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on 6 Apr 2026
4 Night Adventure holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Versey Chicago Lincoln Park
Lakeview
Price was AU$1,828, price is now AU$1,547 per person
AU$1,547
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.6/10 Excellent! (1,483 reviews)
In a good spot in the city, but there were a lot of issues- broken elevator, no exhaust fans in the bathrooms. Had to switch rooms bc the mildew smell in the first was awful. Comfy beds.
Reviewed on 26 Apr 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
Price was AU$3,151, price is now AU$2,251 per person
AU$2,251
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (3,002 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!
Reviewed on 24 Apr 2026
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$3,643, price is now AU$2,845 per person
AU$2,845
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.6/10 Excellent! (2,742 reviews)
Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.
Reviewed on 22 Apr 2026
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge) and a 24-hour health club. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (2,417 reviews)
Grand historic property, conveniently located. Opted for a larger deluxe room, which was a good value. Bathrooms are small bull well appointed. Only critique was daily supplemental activity charge, which was not expected and not a great value.
Reviewed on 28 Apr 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 3 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,066 reviews)
Lovely stay
Reviewed on 23 Apr 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 4 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (3,498 reviews)
great property
Reviewed on 28 Apr 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
