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.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this eco-certified 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.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 20 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 25
found 1 hour ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Institute of Chicago and Chicago Riverwalk are located nearby.
Top Hotel Deals
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
6201 Joliet Rd, Countryside, IL
30.36 km from city center
Stay at this 3.5-star business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the clean rooms ...
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway, Willowbrook, IL
31.67 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. ...
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 ...
Hilton Chicago/Oak Lawn
9333 S Cicero Ave, Oak Lawn, IL
20.44 km from city center
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
30.95 km from city center
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
Hyatt Place Chicago Midway Airport
6550 S Cicero Ave, Chicago, IL
26.07 km from city center
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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. ...
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive, Tinley Park, IL
8.89 km from city center
Stay at this 3.5-star business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful ...
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
6500 S Cicero Ave, Chicago, IL
26.18 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 ...
Hampton Inn by Hilton Chicago-Midway Airport
6540 S Cicero Ave, Chicago, IL
26.13 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 ...
Fairfield Inn and Suites by Marriott Chicago Midway Airport
6630 S Cicero Ave, Chicago, IL
26.01 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 helpful staff and ...
Delta Hotels by Marriott Chicago Willowbrook
7800 Kingery Hwy, Willowbrook, IL
31.28 km from city center
Book a stay at this business-friendly hotel in Willowbrook. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in ...
Extended Stay America Suites Chicago Burr Ridge
15 W. 122nd S. Frontage Rd., Burr Ridge, IL
30.48 km from city center
Book a stay at this business-friendly hotel in Burr Ridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Burr Ridge Village Center and ...
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.
Thu, May 29 - Sun, Jun 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
Mon, Jun 9 - Mon, Jun 16
MCO
Orlando Intl.
MDW
Midway Intl.
$114 Roundtrip, found 4 hours ago
$114
Roundtrip
found 4 hours ago
Sat, Jul 12 - Fri, Jul 18
DEN
Denver Intl.
MDW
Midway Intl.
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Wed, May 14 - Sun, May 25
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
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