
South Side All inclusive Holidays
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Top flight + All inclusive hotel deals in South Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was NZ$4,995, price is now NZ$3,594 per person
NZ$3,594
per person
2 Apr - 9 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on 11 Jan 2026



Level Chicago – Old Town
Downtown Chicago
Price was NZ$5,065, price is now NZ$3,854 per person
NZ$3,854
per person
2 Apr - 9 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on 12 Jan 2026

The Peninsula Chicago
Downtown Chicago
Price was NZ$7,111, price is now NZ$5,493 per person
NZ$5,493
per person
2 Apr - 9 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
5* All inclusive holidays in South Side
Price found within the past 48 hours. Click for updated prices.


The Peninsula Chicago
Downtown Chicago
Price was NZ$7,111, price is now NZ$5,493 per person
NZ$5,493
per person
2 Apr - 9 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
