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Homewood Vacation Packages

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Homewood Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was $332, price is now $217 per person
$217
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $854, price is now $453 per person
$453
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $764, price is now $455 per person
$455
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $622, price is now $382 per person
$382
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
Save 100% on your flight
Price was $603, price is now $376 per person
$376
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (CHI)
Book a stay at this business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dinosaur Discovery Museum and Alpaca Art are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $467, price is now $293 per person
$293
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $390, price is now $254 per person
$254
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $414, price is now $271 per person
$271
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Homewood Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $484, price is now $259 per person
$259
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $670, price is now $355 per person
$355
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $705, price is now $381 per person
$381
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $591, price is now $323 per person
$323
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Homewood Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $614, price is now $339 per person
$339
per person
Jan 23 - Jan 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $854, price is now $453 per person
$453
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $982, price is now $523 per person
$523
per person
Jan 23 - Jan 28
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $624, price is now $342 per person
$342
per person
Feb 1 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Feb 12 - Mon, Feb 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 6 hours ago
$108
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Los Angeles Intl. to O'Hare Intl., returning Mon, Feb 23, priced at $108 found 6 hours ago
Frontier Airlines
Thu, Jan 8 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Los Angeles Intl. to Midway Intl., returning Mon, Jan 12, priced at $195 found 1 day ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$401 Roundtrip, found 1 day ago
$401
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $401 found 1 day ago
TAP Portugal
Sun, Dec 14 - Sun, Dec 14
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$861 Roundtrip, found 4 days ago
$861
Roundtrip
found 4 days ago
Select TAP Portugal flight, departing Sun, Dec 14 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Sun, Dec 14, priced at $861 found 4 days ago