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St. Charles Vacation Packages

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St. Charles Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Price was $317, price is now $201 per person
$201
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The staff is very friendly and professional.

Reviewed on Oct 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $540, price is now $307 per person
$307
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $994, price is now $585 per person
$585
per person
Jan 7 - Jan 13
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.

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $1,907, price is now $1,179 per person
$1,179
per person
Jan 1 - Jan 6
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 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $489, price is now $311 per person
$311
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was $616, price is now $396 per person
$396
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $463, price is now $299 per person
$299
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $575, price is now $374 per person
$374
per person
Dec 28 - Dec 31
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.

St. Charles Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $317, price is now $201 per person
$201
per person
Dec 28 - Dec 31
found 1 day 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 $540, price is now $307 per person
$307
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $444, price is now $272 per person
$272
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $489, price is now $311 per person
$311
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

St. Charles Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $547, price is now $317 per person
$317
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $2,601, price is now $609 per person
$609
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $844, price is now $434 per person
$434
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $690, price is now $384 per person
$384
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Mon, Dec 7 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 4 hours ago
$150
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Los Angeles Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $150 found 4 hours ago
Frontier Airlines
Thu, Nov 19 - Sat, Dec 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$252 Roundtrip, found 9 hours ago
$252
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Nov 19 from Los Angeles Intl. to Midway Intl., returning Sat, Dec 5, priced at $252 found 9 hours ago
Philippine Airlines
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,105 Roundtrip, found 3 hours ago
$1,105
Roundtrip
found 3 hours ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Wed, Dec 2, priced at $1,105 found 3 hours ago
Japan Airlines
Sun, Nov 8 - Mon, Feb 1
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$1,773 Roundtrip, found 9 hours ago
$1,773
Roundtrip
found 9 hours ago
Select Japan Airlines flight, departing Sun, Nov 8 from Hongqiao Intl. to O'Hare Intl., returning Mon, Feb 1, priced at $1,773 found 9 hours ago