Vacations Close To President Obama’s Chicago Family Home

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President Obama’s Chicago Family Home 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
Downtown Chicago
Price was $799, price is now $595 per person
$595
per person
Dec 1 - Dec 6
found 6 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Ok

Reviewed on Oct 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,618, price is now $975 per person
$975
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,034, price is now $1,870 per person
$1,870
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,240, price is now $909 per person
$909
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Not as updated as this pictures look. Quiet which was a plus but the windows were super dirty, the air wasn’t the best which is not as big of a deal in the winter I guess. No microwaved

Reviewed on Oct 7, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $952 per person
$952
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,196, price is now $881 per person
$881
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Nice location, good service and comfortable. Can't say quiet because of loud motor cycles all night through-out downtown. It's a big city and staying downtown comes with a certain level of noise.

Reviewed on Oct 7, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,221, price is now $916 per person
$916
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
All of the above. Great location!

Reviewed on Oct 7, 2026

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,035, price is now $778 per person
$778
per person
Nov 20 - Nov 27
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

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Best Lodging Options Near President Obama’s Chicago Family Home

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
1.19 km from President Obama’s Chicago Family Home
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. ...
Sophy Hyde Park

Sophy Hyde Park

4 out of 5
1411 East 53rd Street Chicago IL
0.79 km from President Obama’s Chicago Family Home
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular ...
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
5225 S Harper Ave Chicago IL
0.93 km from President Obama’s Chicago Family Home
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our ...
Villa Dubois Guest House

Villa Dubois Guest House

2 out of 5
3722 S Calumet Ave Chicago IL
3.09 km from President Obama’s Chicago Family Home
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and a garden. Popular attractions Soldier Field and Grant Park are located nearby.
Best Motel By OYO Chicago I-90

Best Motel By OYO Chicago I-90

2.5 out of 5
6535 S King Dr Chicago IL
3.32 km from President Obama’s Chicago Family Home
Stay at this motel in Chicago. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Wintrust Arena are located ...
Mccormick Place Guest House

Mccormick Place Guest House

3 out of 5
3643 South Indiana Avenue Chicago IL
3.38 km from President Obama’s Chicago Family Home
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and a garden. Popular attractions Soldier Field and Grant Park are located nearby.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.