Vacations Close To Market Square

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Market Square 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 $1,147, price is now $868 per person
$868
per person
Nov 21 - Nov 28
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) 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 $2,708, price is now $1,744 per person
$1,744
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,355, price is now $978 per person
$978
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop

Reviewed on Oct 19, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,385, price is now $1,108 per person
$1,108
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
A party bus pulls up to the

Reviewed on Oct 18, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,779, price is now $1,181 per person
$1,181
per person
Nov 21 - Nov 28
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $1,482, price is now $1,042 per person
$1,042
per person
Nov 21 - Nov 28
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Clean room. Valet service slow.

Reviewed on Oct 18, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,253, price is now $946 per person
$946
per person
Nov 21 - Nov 28
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Had a great night in a great room!

Reviewed on Oct 18, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was $1,407, price is now $1,066 per person
$1,066
per person
Nov 21 - Nov 28
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

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Best Lodging Options Near Market Square

Deer Path Inn

Deer Path Inn

2 out of 5
255 East Illinois Road Lake Forest IL
0.29 km from Market Square
Stay at this hotel in Lake Forest. Enjoy premium bedding and a restaurant. Popular attractions Market Square and Forest Park Beach are located nearby.
Hilton Garden Inn Lake Forest Mettawa

Hilton Garden Inn Lake Forest Mettawa

3 out of 5
26225 North Riverwoods Boulevard Lake Forest IL
5.2 km from Market Square
Book a stay at this golf hotel in Lake Forest. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Sunset Motel

Sunset Motel

2 out of 5
511 Rockland Rd Lake Bluff IL
3.96 km from Market Square
Stay at this motel in Lake Bluff. Enjoy free WiFi, free parking, and a garden. Popular attractions Asylum Skate Park and Middlefork Savanna Forest Preserve are ...
By The Way Motel Lake Bluff

By The Way Motel Lake Bluff

2 out of 5
123 Skokie Hwy Lake Bluff IL
4.22 km from Market Square
Stay at this motel in Lake Bluff. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Asylum Skate Park and Middlefork Savanna Forest ...
The Forester Hotel, part of Unscripted by Hyatt

The Forester Hotel, part of Unscripted by Hyatt

3 out of 5
200 N FIELD DRIVE Lake Forest IL
4.88 km from Market Square
Book a stay at this business-friendly hotel in Lake Forest. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in ...
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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.