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Oglesby Vacation Packages

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Oglesby Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $629, price is now $433 per person
$433
per person
Oct 23 - Oct 26
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.
Great location

Reviewed on Jul 31, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,528, price is now $880 per person
$880
per person
Sep 13 - Sep 16
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.
Excelente hotel, desayuno y ubicación 😉

Reviewed on Jul 31, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,393, price is now $852 per person
$852
per person
Oct 1 - Oct 5
found 1 day 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.
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,258, price is now $823 per person
$823
per person
Sep 13 - Sep 16
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.

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $682, price is now $450 per person
$450
per person
Oct 22 - Oct 25
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.
Enjoyed the stay

Reviewed on Jul 31, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,346, price is now $904 per person
$904
per person
Sep 13 - Sep 16
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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,320, price is now $920 per person
$920
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $683, price is now $476 per person
$476
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Credit Union 1 Amphitheatre and Ravisloe Country Club are located nearby.

Oglesby Vacation Packages 3-4 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 $682, price is now $450 per person
$450
per person
Oct 22 - Oct 25
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 $1,528, price is now $880 per person
$880
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,393, price is now $852 per person
$852
per person
Oct 1 - Oct 5
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 $1,258, price is now $823 per person
$823
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Oglesby Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $974, price is now $564 per person
$564
per person
Sep 30 - Oct 5
found 23 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 $1,711, price is now $953 per person
$953
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,634, price is now $921 per person
$921
per person
Sep 30 - Oct 5
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,634, price is now $2,689 per person
$2,689
per person
Sep 13 - Sep 19
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
Sat, Sep 5 - Tue, Sep 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 5 hours ago
$181
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $181 found 5 hours ago
Bargain Flight
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$244 Roundtrip, just found
$244
Roundtrip
just found
Select Bargain Flight flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $244 just found
Delta
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, just found
$247
Roundtrip
just found
Select Delta flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $247 just found
Hainan Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,128 Roundtrip, found 7 hours ago
$1,128
Roundtrip
found 7 hours ago
Select Hainan Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,128 found 7 hours ago