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Wilmette Vacation Packages

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Wilmette 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 $477, price is now $311 per person
$311
per person
Dec 26 - Dec 30
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $792, price is now $461 per person
$461
per person
Dec 26 - Dec 30
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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $520, price is now $316 per person
$316
per person
Jan 15 - Jan 18
found 10 hours 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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,090, price is now $691 per person
$691
per person
Dec 11 - Dec 17
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $664, price is now $425 per person
$425
per person
Jan 7 - Jan 11
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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $639, price is now $427 per person
$427
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Save 100% on your flight
Price was $802, price is now $537 per person
$537
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, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $480, price is now $327 per person
$327
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
St. Clair hotel lists the room as premium, even though the two windows in the room had no view. Both windows faced the building outter exterior brick walls from all sides. Dim lightning with no direct sunlight, very depressing to look out. The room should have been listened and offered as standard, at best, not premium.

Reviewed on Oct 24, 2026

Wilmette 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 $477, price is now $311 per person
$311
per person
Dec 26 - Dec 30
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
Save 100% on your flight
Price was $792, price is now $461 per person
$461
per person
Dec 26 - Dec 30
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 $520, price is now $316 per person
$316
per person
Jan 15 - Jan 18
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $425 per person
$425
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Wilmette Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $663, price is now $382 per person
$382
per person
Jan 1 - Jan 6
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $409 per person
$409
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,024, price is now $606 per person
$606
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $737, price is now $438 per person
$438
per person
Dec 25 - Dec 30
found 12 hours 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.
$163 Roundtrip, found 6 hours ago
$163
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Los Angeles Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $163 found 6 hours ago
Frontier Airlines
Mon, Nov 9 - Sat, Nov 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$242 Roundtrip, found 4 days ago
$242
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Nov 9 from Los Angeles Intl. to Midway Intl., returning Sat, Nov 21, priced at $242 found 4 days ago
American Airlines
Mon, Dec 7 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$287 Roundtrip, found 6 hours ago
$287
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Mon, Dec 7 from Los Angeles Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $287 found 6 hours ago
Air China
Fri, Nov 13 - Fri, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,125 Roundtrip, found 21 hours ago
$1,125
Roundtrip
found 21 hours ago
Select Air China flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Fri, Nov 27, priced at $1,125 found 21 hours ago