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Hotels in Chicago

Find the best Chicago hotel for your dates, by price or preference

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Prices may change – pop in your dates for the best estimate. Note that prices are based on previous traveller searches and partner prices.
Prices may change – pop in your dates for the best estimate. Note that prices are based on previous traveller searches and partner prices.
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Hotels in Chicago rated best by other travellers

Rated by travellers as the best in the city, these stays are all full marks for cleanliness, customer service and location.
The St. Regis Chicago
1.45 km from city centre
R 8 271
Per night
The Sono Chicago
3.50 km from city centre
R 2 888
Per night
The Peninsula Chicago
2.02 km from city centre
R 10 526
Per night
The St. Regis Chicago
1.45 km from city centre
R 8 271
Per night
The Sono Chicago
3.50 km from city centre
R 2 888
Per night
The Peninsula Chicago
2.02 km from city centre
R 10 526
Per night
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Luxury stay or budget getaway?

Whether you're after 5-star comfort or ease on your wallet, we do the searching so you can sleep easy during your stay in Chicago.

3-star hotels

70 properties
from
R 1 664
per night

4-star hotels

82 properties
from
R 1 433
per night

5-star hotels

13 properties
from
R 3 422
per night

3-star hotels

70 properties
from
R 1 664
per night

4-star hotels

82 properties
from
R 1 433
per night

5-star hotels

13 properties
from
R 3 422
per night

Find a Chicago hotel in the heart of the action

Beat the queues at the top Chicago attractions by staying close to them.

Millennium Park

McCormick Place

Grant Park

Millennium Park

McCormick Place

Grant Park

Fast facts

Sleep easy, armed with the stuff that's good to know before you go.
Highest rated hotelThe St. Regis Chicago – 4.9
Cheapest month to bookMarch
Average 4 star hotel priceR 4,225 per night
Average 5 star hotel priceR 9,274 per night

How to find the best hotel deals in Chicago

Want to use the same magic that powers our award-winning flight search to find the best room rates on the internet? Here are a few tips to help you search and save in seconds.

Flexible on dates? Say hello to better rates

Fancy a break, but haven't decided on exact dates yet? Good! Use our calendar view to find the cheapest month or even day of the month to stay in Chicago.

Finding cheap hotels in Chicago: FAQs

In Chicago, the expected average temperature in March is 3°C. The warmest month is typically July, which averages 26°C. The coolest month is January, with temperatures averaging -8°C. The rainiest month is August, and the driest month is January.

You can always cancel or amend your hotel reservation if you need to, but look out for hotels in Chicago with free cancellation or flexible booking options if you want to protect your money. Some hotels allow you to cancel and get your money back if your plans change.

Of course - the cheapest hotel deal we found within the next seven days is R 671 per night. If you need somewhere in the next 24 hours, we've found you somewhere to stay for R 738 per night.

The average price of a hotel during the week is R 4,371 per night, and the average price on weekends is R 4,629. Overall, it looks like the cheapest day to stay in Chicago could be Sunday.

The nearest airport to Chicago is Chicago Midway Airport (MDW), which is 14.5km from the city centre.

Other airports include:

Chicago O'Hare International Airport, which is 25.4km from the city centre.
Chicago Dupage County Airport, which is 51.2km from the city centre.
Chicago Rockford Airport, which is 126.2km from the city centre.

We crunched some numbers on our calendar and found that Sunday is the cheapest day to stay in Chicago. And the most expensive day seems to be Saturday

The average price of a 3-star hotel in Chicago is currently around <a href="https://www.skyscanner.co.za/hotels/search?entity_id=27544891&checkin=2026-03-29&checkout=2026-03-30&adults=2&rooms=1&sort=-relevance&filters=%7B%22stars%22%3A%223%22%7D" target="_blank" rel="nofollow">R 3,752</a> per night. And the cheapest 3-star hotel we found is R 1,323 per night.

The average price of a 4-star hotel in Chicago is currently around <a href="https://www.skyscanner.co.za/hotels/search?entity_id=27544891&checkin=2026-03-29&checkout=2026-03-30&adults=2&rooms=1&sort=-relevance&filters=%7B%22stars%22%3A%224%22%7D" target="_blank" rel="nofollow">R 4,831</a> per night. And the cheapest 4-star hotel we found is R 671 per night.

The average price of a 5-star hotel in Chicago is currently around <a href="https://www.skyscanner.co.za/hotels/search?entity_id=27544891&checkin=2026-03-29&checkout=2026-03-30&adults=2&rooms=1&sort=-relevance&filters=%7B%22stars%22%3A%225%22%7D" target="_blank" rel="nofollow">R 9,624</a> per night. And the cheapest 5-star hotel we found is R 3,165 per night.

The cheapest month to stay in a hotel in Chicago is April, with an average price of R 4,087 per night. The most expensive month is May, when the average room rate can rise to R 7,803 per night. These average prices are based on all the hotels we found – from hostels through to fancy 5-star hotels.

The average price of a hotel in April is R 4,087 per night, which is around 43% lower than the rest of the year.
If you're planning a trip with the whole family, the best rated hotels for you near Chicago are The Polo Inn Bridgeport U.S.A., The St. Regis Chicago and Hampton Inn & Suites by Hilton Chicago Medical District UIC.

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