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Oak Park Vacation Packages

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Oak Park Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $661, price is now $429 per person
$429
per person
Sep 11 - Sep 13
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. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The only thing that was negative was it took forever to check in and limited parking by the lobby entrance.

Reviewed on Aug 7, 2026

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
Price was $822, price is now $470 per person
$470
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Price was $4,740, price is now $2,744 per person
$2,744
per person
Sep 13 - Sep 19
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 in our reviews. Popular attractions Michigan Avenue 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 $1,224, price is now $761 per person
$761
per person
Oct 22 - Oct 25
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 $1,332, price is now $831 per person
$831
per person
Oct 15 - Oct 19
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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,423, price is now $900 per person
$900
per person
Oct 14 - Oct 18
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.
Great staff, great place!

Reviewed on Aug 5, 2026

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $1,060, price is now $676 per person
$676
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The breakfast was very minimal.

Reviewed on Aug 7, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,378, price is now $905 per person
$905
per person
Oct 14 - Oct 18
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.

Oak Park Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $822, price is now $470 per person
$470
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $859, price is now $515 per person
$515
per person
Sep 6 - Sep 9
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 $1,224, price is now $761 per person
$761
per person
Oct 22 - Oct 25
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 $1,332, price is now $831 per person
$831
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Oak Park Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,630, price is now $930 per person
$930
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,255, price is now $1,220 per person
$1,220
per person
Oct 19 - Oct 26
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
Price was $3,285, price is now $1,826 per person
$1,826
per person
Sep 13 - Sep 19
found 1 day 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 $4,740, price is now $2,744 per person
$2,744
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, Aug 29 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 14 hours ago
$171
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $171 found 14 hours ago
Delta
Tue, Sep 22 - Tue, Sep 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 22 from Los Angeles Intl. to Midway Intl., returning Tue, Sep 29, priced at $220 found 2 days ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 4 days ago
$250
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $250 found 4 days ago
Hainan Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,131 Roundtrip, found 4 days ago
$1,131
Roundtrip
found 4 days ago
Select Hainan Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,131 found 4 days ago