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

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star 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.

Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 Millennium Park and Art Institute of Chicago are located nearby.

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this 4-star 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.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 21 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Top Hotel Deals

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive, Tinley Park, IL
29.1 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 ...

Super 8 by Wyndham South Holland
17225 Halsted St, South Holland, IL
20.07 km from city center
Book a stay at this business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...

Holiday Inn Express & Suites Chicago - Oak Forest by IHG
4365 Frontage Rd, Oak Forest, IL
26.17 km from city center
Stay at this hotel in Oak Forest. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Popular attractions George Dunne National Golf Club and Oak Hill ...

DoubleTree by Hilton Chicago - Alsip
5000 W 127th St, Alsip, IL
32.79 km from city center
Stay at this 4-star business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

Fairfield Inn and Suites By Marriott Merrillville
8275 Georgia St, Merrillville, IN
12.14 km from city center
Book a stay at this business-friendly hotel in Merrillville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Wingate by Wyndham Tinley Park
18421 N Creek Drive, Tinley Park, IL
29.61 km from city center
Stay at this hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...

Luxe Inn and Suites
1335 E. SIBLEY BLVD., Dolton, IL
21.36 km from city center
Stay at this motel in Dolton. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Veterans Memorial Park and River Oaks Center are located ...

Admiral Motel By Oyo Chicago I-94
9118 S Cottage Grove Ave, Chicago, IL
32.96 km from city center
Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Chicago Museum of Science and Industry and Jackson ...

Baymont by Wyndham Chicago/Alsip
12801 South Cicero, Alsip, IL
32.15 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 ...

Motel 6 Hammond, IN - Chicago Area
3840 179th St, Hammond, IN
13.6 km from city center
Stay at this motel in Hammond. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...

La Quinta Inn & Suites by Wyndham South Holland
610 Tollview Dr, South Holland, IL
19.76 km from city center
Stay at this 3-star business-friendly hotel in South Holland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in ...

Ameristar Casino Hotel East Chicago
777 Ameristar Blvd., East Chicago, IN
22.6 km from city center
Stay at this 4-star beach hotel in East Chicago. Enjoy 5 restaurants, a marina, and a casino. Our guests praise the helpful staff and the clean rooms in our ...

La Quinta Inn & Suites by Wyndham Chicago Tinley Park
7255 West 183rd St., Tinley Park, IL
29.55 km from city center
Stay at this 3-star business-friendly hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.

Tue, Jun 24 - Tue, Jul 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$107 Roundtrip, found 6 days ago
$107
Roundtrip
found 6 days ago

Mon, Jun 23 - Mon, Jun 30
DEN
Denver Intl.
MDW
Midway Intl.
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago

Thu, Aug 28 - Sun, Aug 31
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago

Fri, Jun 27 - Fri, Jul 4
IAH
George Bush Intercontinental
MDW
Midway Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
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