Serena Vacations

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Serena Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
Save 100% on your flight
$1,087
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I stayed a weekend at the hotel and upon entering there is a restaurant. The hotel check in is upstairs. I’m not a fan of that setup because I was confused as to where to go when my Lyft dropped me off. The staff is very nice and friendly. They interacted with guests in passing. In my room there was noticeable wear and tear. Overall the room was clean. I used the spa. You have to book with them for them to open the spa. It seems like a company rents the space out and comes to service you as needed. I enjoyed my spa experience. Lastly, the restaurant was okay. It didn’t have enough variety for me but the tomato soup and cheesecake I enjoyed.

Reviewed on Sep 3, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$1,189
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!

Reviewed on Sep 2, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$1,212
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
O

Reviewed on Sep 2, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

Downtown Chicago
Save 100% on your flight
$1,168
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
$1,159
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Room was very clean, staff extremely helpful, and in a perfect part of town for walking anywhere

Reviewed on Sep 3, 2026

Stay One Chicago

Stay One Chicago

Downtown Chicago
Save 100% on your flight
$1,607
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, private pools, and 3 restaurants. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

2643 IL-178 Utica IL
30.09 km from city center
Book a stay at this golf hotel in Utica. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ...
Days Inn by Wyndham Oglesby/ Starved Rock

Days Inn by Wyndham Oglesby/ Starved Rock

120 N Lewis Ave Oglesby IL
35.84 km from city center
Book a stay at this business-friendly hotel in Oglesby. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

1879 N 2703rd Rd Ottawa IL
18.35 km from city center
Stay at this cabin in Ottawa. Enjoy free parking, patios, and climate control. Popular attractions Tangled Roots Brewing Company - The Lone Buffalo and Washington ...
Super 8 by Wyndham Yorkville

Super 8 by Wyndham Yorkville

1510 A North Bridge St Yorkville IL
30.76 km from city center
Book a stay at this business-friendly motel in Yorkville. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
The Montcler Hotel - Redberri Luxury Collection

The Montcler Hotel - Redberri Luxury Collection

3300 Drew Ave Sandwich IL
22.48 km from city center
Book a stay at this business-friendly hotel in Sandwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Farnsworth House and Silver Springs ...
Comfort Inn Morris I-80

Comfort Inn Morris I-80

70 Gore Rd Morris IL
27.73 km from city center
Book a stay at this business-friendly hotel in Morris. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Super 8 by Wyndham Ottawa Starved Rock

Super 8 by Wyndham Ottawa Starved Rock

500 East Etna Rd. Ottawa IL
15.33 km from city center
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms ...
Super 8 by Wyndham Morris

Super 8 by Wyndham Morris

70 Green Acres Dr Morris IL
28.02 km from city center
Book a stay at this business-friendly motel in Morris. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Echo Bowling Lanes and Grundy County ...
Holiday Inn Express & Suites Yorkville by IHG

Holiday Inn Express & Suites Yorkville by IHG

577 E KENDALL DRIVE Yorkville IL
30.72 km from city center
Book a stay at this spa hotel in Yorkville. Enjoy free breakfast, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Quality Inn & Suites Mendota near I-39

Quality Inn & Suites Mendota near I-39

1307 Kailash Dr Mendota IL
28.77 km from city center
Stay at this hotel in Mendota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tri-County ...
Best Western Oglesby Inn

Best Western Oglesby Inn

900 Holiday Street Oglesby IL
36.05 km from city center
Book a stay at this business-friendly hotel in Oglesby. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
Comfort Inn Ottawa Starved Rock Area

Comfort Inn Ottawa Starved Rock Area

120 W. Stevenson Road Ottawa IL
14.88 km from city center
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Days Inn & Suites by Wyndham Morris/I-80

Days Inn & Suites by Wyndham Morris/I-80

80 Hampton Road Morris IL
27.68 km from city center
Book a stay at this business-friendly hotel in Morris. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Hampton Inn Yorkville

Hampton Inn Yorkville

310 East Countryside Parkway Yorkville IL
31.16 km from city center
Book a stay at this business-friendly hotel in Yorkville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express & Suites Ottawa by IHG

Holiday Inn Express & Suites Ottawa by IHG

2850 Columbus Street Ottawa IL
15.45 km from city center
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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