Vacations Close To Hoosier Prairie

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Hoosier Prairie Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $799, price is now $595 per person
$595
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Showing its age....grubby interior, windows need a good clean. Only 1 lift out of 4 working.Bed bases in queen room project out beyond the mattress...more than a few swear words as repeatedly catching knees on the corners. Convenient location

Reviewed on Oct 8, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,618, price is now $975 per person
$975
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Everything was great. Provide microwaves.

Reviewed on Oct 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,034, price is now $1,870 per person
$1,870
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,240, price is now $909 per person
$909
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
A

Reviewed on Oct 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $952 per person
$952
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,196, price is now $881 per person
$881
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Room service is very quick

Reviewed on Oct 8, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,221, price is now $916 per person
$916
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,035, price is now $778 per person
$778
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Clean room with comfortable beds. Roomy for traveling with another person. Lobby coffee was a bonus! They even loaned us umbrellas on the rainy sightseeing day.

Reviewed on Oct 8, 2026

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Best Lodging Options Near Hoosier Prairie

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
35.63 km from Hoosier Prairie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
36.75 km from Hoosier Prairie
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
39.13 km from Hoosier Prairie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
41.73 km from Hoosier Prairie
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Jaslin Hotel

Jaslin Hotel

3 out of 5
261 West Cermak Rd Chicago IL
39.68 km from Hoosier Prairie
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
41.46 km from Hoosier Prairie
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
41.13 km from Hoosier Prairie
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE Chicago IL
41.35 km from Hoosier Prairie
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests ...
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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.