Photo by Susie Morgan
Hotels in Prairie District
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Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop3.0 star property
The Loop, 1.3 km from Prairie District
8.8 out of 10, Excellent, (1763)
8.8/10
Excellent
(1763)
The price is $73
$73
$86 total
includes taxes & fees
Jan 5 - Jan 6, 2026
8.4 out of 10, Very Good, (2382)
8.4/10
Very Good
(2382)
The price is $114
$114
$134 total
includes taxes & fees
Dec 24 - Dec 25
Best Western Grant Park Hotel
Best Western Grant Park Hotel2.5 star property
The Loop, 1.3 km from Prairie District
8.2 out of 10, Very Good, (2650)
8.2/10
Very Good
(2650)
The price is $72
$72
$85 total
includes taxes & fees
Jan 5 - Jan 6, 2026
8.0 out of 10, Very Good, (9672)
8.0/10
Very Good
(9672)
The price is $100
$100
$118 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel4.0 star property
The Loop, 2 km from Prairie District
9.6 out of 10, Exceptional, (1122)
9.6/10
Exceptional
(1122)
The price is $95
$95
$112 total
includes taxes & fees
Jan 6 - Jan 7, 2026
8.0 out of 10, Very Good, (2650)
8.0/10
Very Good
(2650)
The price is $59
$59
$86 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop3.0 star property
The Loop, 1.3 km from Prairie District
8.8 out of 10, Excellent, (2147)
8.8/10
Excellent
(2147)
The price is $81
$81
$95 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago4.0 star property
Theatre District, 2.5 km from Prairie District
8.8 out of 10, Excellent, (3320)
8.8/10
Excellent
(3320)
The price is $74
$74
$87 total
includes taxes & fees
Dec 30 - Dec 31
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago2.0 star property
The Loop, 1.9 km from Prairie District
7.4 out of 10, Good, (2499)
7.4/10
Good
(2499)
The price is $77
$77
$90 total
includes taxes & fees
Dec 21 - Dec 22
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, Chicago4.0 star property
The Loop, 3.4 km from Prairie District
8.8 out of 10, Excellent, (1992)
8.8/10
Excellent
(1992)
The price is $82
$82
$96 total
includes taxes & fees
Dec 30 - Dec 31
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown4.0 star property
Theatre District, 2.7 km from Prairie District
9.2 out of 10, Wonderful, (2127)
9.2/10
Wonderful
(2127)
The price is $101
$101
$149 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel4.0 star property
Theatre District, 2.6 km from Prairie District
8.4 out of 10, Very Good, (2144)
8.4/10
Very Good
(2144)
The price is $111
$111
$155 total
includes taxes & fees
Dec 24 - Dec 25
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop4.0 star property
Theatre District, 2.9 km from Prairie District
9.4 out of 10, Exceptional, (1012)
9.4/10
Exceptional
(1012)
The price is $107
$107
$155 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cambria Hotel Chicago Loop - Theatre District
Cambria Hotel Chicago Loop - Theatre District4.0 star property
Theatre District, 3 km from Prairie District
8.8 out of 10, Excellent, (1456)
8.8/10
Excellent
(1456)
The price is $87
$87
$102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hyatt Centric The Loop Chicago
Hyatt Centric The Loop Chicago4.0 star property
Theatre District, 2.7 km from Prairie District
9.0 out of 10, Wonderful, (2307)
9.0/10
Wonderful
(2307)
The price is $115
$115
$135 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Majestic Chicago Theatre District
Hampton Inn Majestic Chicago Theatre District3.0 star property
Theatre District, 2.7 km from Prairie District
9.0 out of 10, Wonderful, (1001)
9.0/10
Wonderful
(1001)
The price is $93
$93
$110 total
includes taxes & fees
Dec 28 - Dec 29
The Allegro Royal Sonesta Hotel Chicago Loop
The Allegro Royal Sonesta Hotel Chicago Loop4.0 star property
Theatre District, 3.1 km from Prairie District
9.0 out of 10, Wonderful, (2308)
9.0/10
Wonderful
(2308)
The price is $97
$97
$146 total
includes taxes & fees
Jan 15 - Jan 16, 2026
8.6 out of 10, Excellent, (1942)
8.6/10
Excellent
(1942)
The price is $74
$74
$87 total
includes taxes & fees
Dec 30 - Dec 31
Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central Loop3.0 star property
The Loop, 2.5 km from Prairie District
9.2 out of 10, Wonderful, (1260)
9.2/10
Wonderful
(1260)
The price is $106
$106
$124 total
includes taxes & fees
Dec 24 - Dec 25
8.8 out of 10, Excellent, (4861)
8.8/10
Excellent
(4861)
The price is $82
$82
$96 total
includes taxes & fees
Dec 30 - Dec 31
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.
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.
When is the best time to visit Chicago?
When is the best time to visit Chicago?Our prices for hotels in Chicago are cheapest in January
When is the best time to visit Chicago?
When is the best time to visit Chicago?
Our prices for hotels in Chicago are cheapest in January
Price trends for hotels in Chicago
Pricing is based on two traveler single night rates
Currently viewing crowd sizes and weather for December.
Typical weather for Chicago
December
High crowds
High 3°C / low -2°C. Cloudy most days.
View properties in December 3°
December, High crowds, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
-1°
January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
0°
February, Low crowds, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
6°
March, Low crowds, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
0°
11°
April, Low crowds, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
17°
May, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
23°
June, High crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
26°
July, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
26°
August, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
20°
23°
September, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
16°
October, Moderate crowds, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
8°
November, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
Monthly weather averages (˚C)
Top landmarks in Prairie District
Clarke House Museum
If museums are on your list of things to see, you might want to browse the collections at Clarke House Museum in Near South Side. Our travelers also like the art galleries and monuments in the area. If you want to see more of the museums in Chicago, you can easily walk to National Vietnam Veterans Art Museum or Glessner House Museum.
National Vietnam Veterans Art Museum
National Vietnam Veterans Art Museum is just one of the attractions in Near South Side, Chicago so you might want to stop by during your trip. If you want to experience more of the culture Chicago has to offer, head to Michigan Avenue, Wintrust Arena, and Soldier Field.
Check out reviews of Prairie District hotels guests love
Sable at Navy Pier Chicago, Curio Collection by Hilton
10/10 Excellent
"Staff was courteous and accommodating. Rooms were clean with a beautiful view."
InterContinental Chicago Magnificent Mile by IHG
10/10 Excellent
"Room was spotless. "
Congress Plaza Hotel
10/10 Excellent
"Room was comfortable and clean. Staff was very friendly "
River Hotel
10/10 Excellent
"Very nice hotel"
Hilton Chicago/Magnificent Mile Suites
10/10 Excellent
"Awesome "
Silversmith Hotel Chicago Downtown
10/10 Excellent
"Didn't eat breakfast at the hotel cause went to wildberry pancakes and Cafe but everything else was great"
Swissotel - Chicago
10/10 Excellent
"Did not have breakfast. "
Hyatt Regency Chicago
10/10 Excellent
"Staff were friendly, rooms clean, and appreciated the $25 food credit each night of the stay. "
The Whitehall Hotel, BW Premier Collection
10/10 Excellent
"Clean, great staff"
Find out more about Prairie District