Plano Vacations

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Plano 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.
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.
Everything was clean, staff was friendly, and breakfast was yummy :)

Reviewed on Sep 3, 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.
n/a

Reviewed on Sep 3, 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.
Estuve 3 días hospedada y nunca limpiaron la habitación

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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Top Hotel Deals

Hollywood Casino Aurora

Hollywood Casino Aurora

2500 N Farnsworth Ave Aurora IL
26.41 km from city center
Book a stay at this spa hotel in Aurora. Enjoy a full-service spa, 9 restaurants, and a 24-hour fitness center. Popular attractions Chicago Premium Outlets and ...
Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL
37.59 km from city center
Stay at this motel in Naperville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn Express & Suites Aurora - Naperville by IHG

Holiday Inn Express & Suites Aurora - Naperville by IHG

111 North Broadway Avenue Aurora IL
21.69 km from city center
Book a stay at this business-friendly hotel in Aurora. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Red Roof Inn PLUS+ Chicago - Naperville

Red Roof Inn PLUS+ Chicago - Naperville

1698 West Diehl Road Naperville IL
31.49 km from city center
Stay at this hotel in Naperville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hotel Arista

Hotel Arista

2139 City Gate Ln Naperville IL
32.17 km from city center
Book a stay at this luxury hotel in Naperville. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Wingate by Wyndham - Joliet

Wingate by Wyndham - Joliet

101 McDonald Avenue Joliet IL
33.24 km from city center
Book a stay at this business-friendly hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Geneva Motel Inn

Geneva Motel Inn

100 South Tyler Rd St. Charles IL
34.84 km from city center
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Best Western Naperville Inn

Best Western Naperville Inn

1617 Naperville Wheaton Rd Naperville IL
37.72 km from city center
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Chicago/Naperville/Warrenville

Hyatt Place Chicago/Naperville/Warrenville

27576 Maecliff Dr Warrenville IL
35.32 km from city center
Book a stay at this business-friendly hotel in Warrenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Comfort Inn Romeoville - Bolingbrook

Comfort Inn Romeoville - Bolingbrook

1235 Lake View Drive Romeoville IL
34.53 km from city center
Book a stay at this business-friendly hotel in Romeoville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Country Inn & Suites by Radisson Romeoville I-55

Country Inn & Suites by Radisson Romeoville I-55

1265 Lakeview Dr Romeoville IL
34.45 km from city center
Book a stay at this business-friendly hotel in Romeoville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hotel Indigo Naperville Riverwalk by IHG

Hotel Indigo Naperville Riverwalk by IHG

120 Water Street Naperville IL
34.26 km from city center
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean ...
Hampton Inn Joliet-Plainfield I-55

Hampton Inn Joliet-Plainfield I-55

3555 Mall Loop Drive Joliet IL
31.75 km from city center
Stay at this hotel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Hampton Inn Chicago/Naperville

Hampton Inn Chicago/Naperville

1087 E Diehl Rd Naperville IL
37.19 km from city center
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Motel 6 Joliet, IL - Chicago - I-55

Motel 6 Joliet, IL - Chicago - I-55

3551 Mall Loop Dr Joliet IL
31.8 km from city center
Stay at this motel in Joliet. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
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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.