
Flossmoor Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Flossmoor Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $1,059, price is now $817 per person
$817
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.
The room was not ready upon arrival so we had to wait 45 min after check in to get into our room. Additionally, we left the room at 930a , returned at 6p and the room had not been cleaned. There were fresh towels laid on top of the bed but nothing else had been touched. Seemed a little disorganized bc when we asked why the room had been left untouched they said “they were just really busy bc they were booked” but idk, if I’m paying to stay there, it’s not my job to make sure you can handle the level of occupancy you booked. It’s pretty centrally located but I wouldn’t stay here again
Reviewed on Nov 15, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,606, price is now $1,102 per person
$1,102
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.
Top notch hotel. Never stayed at a Riu property before, but will definitely look into one whenever I am out of town. Clean, modern, and spacious rooms, terrific customer service and the breakfast buffet was very good too.
Reviewed on Nov 15, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was $1,576, price is now $1,136 per person
$1,136
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) 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.

The Blackstone, Autograph Collection
Downtown Chicago
Price was $1,126, price is now $829 per person
$829
per person
Dec 24 - Dec 31
found 16 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Swissotel - Chicago
Downtown Chicago
Price was $1,323, price is now $1,012 per person
$1,012
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Beautiful building Nice room sweet customer services. The no microwave and charging customers to warm their food is honestly insane and inconsiderate. It was a 5/10 probably will not be a returning customer.
Reviewed on Nov 15, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $1,080, price is now $829 per person
$829
per person
Dec 21 - Dec 28
found 20 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
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Reviewed on Nov 12, 2026
Top Hotel Deals

Wind Creek Chicago Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
5.32 km from city center
Book a stay at this luxury resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Ravisloe Country Club and Oak Hill ...

William Tell Hotel MOD Collection by Sonesta
6201 Joliet Rd Countryside IL
30.42 km from city center
Book a stay at this business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the clean ...

Motel 6 Bridgeview, IL
9625 S 76th Ave Bridgeview IL
21.85 km from city center
Stay at this motel in Bridgeview. 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 Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
24.51 km from city center
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 ...

DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
14.26 km from city center
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
25.93 km from city center
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 ...

Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
31.64 km from city center
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. ...

The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
30.92 km from city center
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 ...

Baymont by Wyndham Chicago/Alsip
12801 South Cicero Alsip IL
13.63 km from city center
Book a stay at this business-friendly hotel in Alsip. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave Chicago IL
26.2 km from city center
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 ...

Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
30.39 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...

Courtyard by Marriott Chicago Midway Airport
6610 S Cicero Ave Chicago IL
26.02 km from city center
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 ...

Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
19.08 km from city center
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Martin Luther King Drive and Marquette Park are located ...
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.

Wed, Dec 16 - Wed, Dec 30
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago

Wed, Dec 16 - Wed, Dec 30
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$153 Roundtrip, found 4 days ago
$153
Roundtrip
found 4 days ago

Tue, Dec 15 - Sat, Dec 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$169 Roundtrip, found 4 days ago
$169
Roundtrip
found 4 days ago

Wed, Dec 16 - Wed, Dec 30
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago

