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Oak Park Vacation Packages

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A historic house with a porch, a tower, and a sign indicating it is the birthplace of Ernest Hemingway.

Oak Park
Chicago
Illinois
United States of America
North America
Hotwire.com

Oak Park Flight + Hotel Packages

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

The Glen Club

4 out of 5

Save 100% on your flight

Price was $463, price is now $308 per person

$308

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and The Glen Town Center are located nearby.

Level Chicago – Old Town

4 out of 5

Save 100% on your flight

Price was $1,119, price is now $652 per person

$652

per person

Dec 31 - Jan 5

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.

The stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Sheraton Grand Chicago Riverwalk

4 out of 5

Save 100% on your flight

Price was $683, price is now $452 per person

$452

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Ant infestation

Reviewed on Oct 16, 2026

Pendry Chicago

4.5 out of 5

Save 100% on your flight

Price was $866, price is now $574 per person

$574

per person

Dec 17 - Dec 20

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.

Hotel Riu Plaza Chicago

4 out of 5

Save 100% on your flight

Price was $532, price is now $357 per person

$357

per person

Dec 4 - Dec 6

found 2 days 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.

Trump International Hotel & Tower Chicago

5 out of 5

Save 100% on your flight

Price was $1,093, price is now $746 per person

$746

per person

Jan 8 - Jan 12

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.

Clean space to relax and enjoy your trip

Reviewed on Oct 15, 2026

Park Hyatt Chicago

5 out of 5

Save 100% on your flight

Price was $1,643, price is now $1,121 per person

$1,121

per person

Dec 29 - Jan 2

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.

Excellent experience. I’d recommend this property for their outstanding service and updated rooms.

Reviewed on Oct 9, 2026

Lodge Geneva National

4 out of 5

Price was $764, price is now $531 per person

$531

per person

Nov 19 - Nov 23

found 2 hours ago

Roundtrip flight included

Phoenix (PHX) to Chicago (ORD)

Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Lake Como are located nearby.