Eola Vacations
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Eola Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$595
per person
Dec 1 - Dec 6
found 22 hours 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.
Functional and I got what I needed
Reviewed on Oct 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$975
per person
Nov 20 - Nov 27
found 21 hours ago
Roundtrip 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.
Great views, terrible service. Unfortunately I did not enjoy my stay because of the overwhelming rudeness of the staff. The front desk looked around as I approached, both arriving and checking out. Fully staffed but I had to alert them I was standing there. The bell hops were excellent. Very friendly. As well as the bartender in the lobby and the waitress on the rooftop. However everyone else not so much. Please work with your frit dosk staffers. As they set the tone.
Reviewed on Oct 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,870
per person
Nov 20 - Nov 27
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
$909
per person
Nov 20 - Nov 27
found 21 hours ago
Roundtrip 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.
Not as updated as this pictures look. Quiet which was a plus but the windows were super dirty, the air wasn’t the best which is not as big of a deal in the winter I guess. No microwaved
Reviewed on Oct 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$952
per person
Nov 20 - Nov 27
found 21 hours ago
Roundtrip 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.
Arlo Chicago
Downtown Chicago
$881
per person
Nov 20 - Nov 27
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Room service is very quick
Reviewed on Oct 8, 2026
Top Hotel Deals
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
Sybaris Pool Suites
600 Ogden Ave Downers Grove IL
Stay at this hotel in Downers Grove. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Oakbrook Center Mall and Ty Warner Park are ...
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
Book a stay at this boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
Hilton Chicago/Oak Brook Hills Resort & Conference Center
3500 Midwest Road Oak Brook IL
Book a stay at this spa resort in Oak Brook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...
Hollywood Casino Aurora
2500 N Farnsworth Ave Aurora IL
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 ...
Hyatt Place Itasca
1150 North Arlington Heights Road Itasca IL
Book a stay at this business-friendly hotel in Itasca. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Westin Chicago Lombard
70 Yorktown Center Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Geneva Motel Inn
100 South Tyler Rd St. Charles IL
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. ...
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hyatt Place Chicago/Lombard/Oak Brook
2340 South Fountain Square Drive Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn Joliet-Plainfield I-55
3555 Mall Loop Drive Joliet IL
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 ...
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.
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177
Roundtrip
found 14 hours ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177
Roundtrip
found 14 hours ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$177
Roundtrip
found 14 hours ago
Mon, Nov 9 - Wed, Nov 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$177
Roundtrip
found 1 day ago
Sat, Nov 14 - Mon, Nov 16
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200
Roundtrip
just found
Best points of interest in Chicago
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