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Chicago Romantic Hotels

Search and compare hundreds of travel sites at once for romantic hotels in Chicago, Illinois

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Best Chicago romantic hotels

Most recommended Chicago romantic hotels

Show all
The Peninsula Chicago - Chicago - Patio
The Peninsula Chicago
Near North Side
9.4Wonderful(562)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£656+
Check availability
The Langham Chicago - Chicago - Lounge
The Langham Chicago
Near North Side
9.4Wonderful(921)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£573+
Check availability
Viceroy Chicago - Chicago - Restaurant
Viceroy Chicago
Near North Side
9.1Wonderful(1393)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£359+
Check availability
Loews Chicago Hotel - Chicago - Bedroom
Loews Chicago Hotel
Near North Side
9.1Wonderful(2065)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£362+
Check availability
Trump International Hotel & Tower Chicago - Chicago - Building
Trump International Hotel & Tower Chicago
Near North Side
9.1Wonderful(2067)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
£446+
Check availability
Residence Inn by Marriott Chicago Downtown/Loop - Chicago - Bar
Residence Inn by Marriott Chicago Downtown/Loop
Downtown
9.0Wonderful(1023)
Free Wi-Fi
Pet-friendly
Air conditioning
£290+
Check availability
Kimpton Gray Hotel - Chicago - Bar
Kimpton Gray Hotel
Downtown
8.9Very Good(655)
Pet-friendly
Air conditioning
£353+
Check availability
Staypineapple, An Iconic Hotel, The Loop - Chicago - Living room
Staypineapple, An Iconic Hotel, The Loop
Downtown
8.9Very Good(1814)
Free Wi-Fi
Pet-friendly
Air conditioning
£262+
Check availability
Sofitel Chicago Magnificent Mile - Chicago - Patio
Sofitel Chicago Magnificent Mile
Near North Side
8.9Very Good(2676)
Free Wi-Fi
Pet-friendly
Air conditioning
£275+
Check availability
LondonHouse Chicago, Curio Collection by Hilton - Chicago - Lounge
LondonHouse Chicago, Curio Collection by Hilton
Downtown
8.9Very Good(2072)
Free Wi-Fi
Air conditioning
£328+
Check availability
Eurostars Magnificent Mile - Chicago - Living room
Eurostars Magnificent Mile
Near North Side
8.8Very Good(2459)
Free Wi-Fi
Air conditioning
£189+
Check availability
Royal Sonesta Chicago Downtown - Chicago - Building
Royal Sonesta Chicago Downtown
Downtown
8.7Very Good(3227)
Pet-friendly
Air conditioning
£257+
Check availability
Thompson Chicago - Chicago - Living room
Thompson Chicago
Near North Side
8.7Very Good(553)
Free Wi-Fi
Pet-friendly
Air conditioning
£276+
Check availability
theWit Chicago, a Hilton Hotel - Chicago - Lounge
theWit Chicago, a Hilton Hotel
Downtown
8.7Very Good(940)
Pet-friendly
Air conditioning
£301+
Check availability
Hyatt Regency Chicago - Chicago - Bedroom
Hyatt Regency Chicago
Downtown
8.7Very Good(5878)
Free Wi-Fi
Air conditioning
£310+
Check availability
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KAYAK’s insights for romantic hotels in Chicago

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chicago with confidence.

Which month has the cheapest hotel for couples rates in Chicago?

Hotels for couples are cheapest in Chicago in May, with average rates of £79. In comparison, October is the most expensive month, with prices at £283.

What is the cheapest day of the week to book a hotel for couples in Chicago?

Monday offers the lowest rates in Chicago, with an average nightly price of £96. The highest prices are found on Wednesday, with average rates at £297.

Which neighbourhood do KAYAK users most love to book their hotel for couples in Chicago?

The most popular neighbourhood in Chicago among KAYAK users to search for a hotel for couples is Downtown, with an average price of £174. River Hotel, Central Loop Hotel, and Congress Plaza Hotel rank among the highest-rated hotels in Downtown.

How much is a hotel for couples in Chicago for tonight?

The best deal for a 3-star hotel for couples room in Chicago found by KAYAK users in the last 3 days was £129, while a 4-star hotel for couples the lowest price was £103. The cheapest room found overall was for £103.

How much is a hotel for couples in Chicago for this weekend?

The cheapest hotel for couples room in Chicago for the upcoming weekend found on KAYAK in the last 3 days was for £97 per night. For the same dates, 3-star hotel for couples rooms have been found for as low as £100 per night and 4-star hotel for couples rooms from £97 per night.

How early should you book a hotel in Chicago?

Book at least 58 days before your stay begins to get the best price for your Chicago hotel.
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Good to know

Low season

May

High season

October

Average price (weeknight)

£254

Average price (weekend night)

£190
Cheapest month to stay with an average 37% drop in price.
Most expensive month to stay with an average 123% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chicago romantic hotel deals

  • Prices for romantic hotels in Chicago are cheaper in the low season, which is in May and February.
  • Romantic room prices can vary depending on different factors. However, generally, rooms cost less on a Monday. The most expensive night for a stay is Wednesday.
  • The cheapest romantic hotel room in Chicago found on KAYAK in the last 2 weeks was £106. The most expensive cost £106.

FAQs about Chicago romantic hotels

  • How much does a room in a romantic hotel in Chicago cost?

    On average, romantic hotel rooms in Chicago cost £271. Depending on when you make your booking, when you book for, and other factors, it is possible to get better deals. The cheapest price booked on KAYAK in the last 3 days was £128.

Where to stay in a romantic hotel in Chicago?

Our map will help you find the perfect place to stay in Chicago by showing you the exact location of each hotel.

Everything you need to know for your stay in Chicago

Chicago Romantic Hotel Deals. Search for romantic hotels in Chicago. Find the best hotel rooms for couples in Chicago. KAYAK searches hundreds of travel sites to help you find romantic hotels and book the room that suits you best.

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