Vacations Close To Maxwell Street Market

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Maxwell Street Market 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
Save 100% on your flight
Price was $963, price is now $674 per person
$674
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,893, price is now $1,118 per person
$1,118
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Everything was awesome but there was no microwave and we needed one

Reviewed on Oct 3, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,369, price is now $1,487 per person
$1,487
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,384, price is now $990 per person
$990
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,384, price is now $1,013 per person
$1,013
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Good location and parking, but the room has poor soundproofing, we can here the noise from outside

Reviewed on Oct 2, 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 $1,240, price is now $917 per person
$917
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,343, price is now $997 per person
$997
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $971, price is now $727 per person
$727
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Slight wear and tear on the furniture dates the place and I wish the rooms were brighter, but excellent location and great value. Loved the shower!

Reviewed on Oct 2, 2026

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Best Lodging Options Near Maxwell Street Market

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
1.82 km from Maxwell Street Market
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
0.86 km from Maxwell Street Market
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
2.72 km from Maxwell Street Market
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
1.66 km from Maxwell Street Market
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
1.63 km from Maxwell Street Market
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
1.68 km from Maxwell Street Market
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
LIVN - West Loop Chicago

LIVN - West Loop Chicago

4 out of 5
555 West Jackson Boulevard Chicago IL
1.18 km from Maxwell Street Market
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and laundry facilities. Popular attractions Millennium Park and Chicago Riverwalk are ...
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
1.71 km from Maxwell Street Market
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 ...
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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.