What's the cheapest luxury hotel in Chicago right now?

The lowest real live rate we found is €356 a night (sample dates, about a month out) — see the listings above, or search your own dates for the current price.

Do luxury hotels in Chicago include free wifi and breakfast?

Of the live listings we checked, 52% include free wifi and 43% include breakfast — check each hotel's own listing for exact inclusions before booking.

When's the best time to visit Chicago?

Based on real historical weather data, October tends to have the mildest conditions — see the weather section above for the full breakdown.

How do I book a hotel in Chicago?

Use the search box above with your exact check-in and check-out dates to see live availability and pricing, then book directly with our partner — we don't add any fee on top.

Search hotels in Chicago

Compare flights, hotels, cars, and activities for this trip in one place.

500+airlines & travel sites compared

21,000+routes tracked

€0booking fees from us

Freeprice drop alerts

Luxury Hotels in Chicago

United States, Americas

€458

Average nightly rate

€356

Cheapest on file

Live listings found

52%

Include free wifi

We found 21 real live luxury hotel listings in Chicago, ranging from €356 to €712 a night. Chicago is located in United States, in Americas. Prices shown are a live sample for a 1-night stay starting 2026-08-22; use the search box above for your own dates.

Live luxury hotel listings in Chicago

The Wade

★ 8.2(110)· 4.5★ hotel· Breakfast incl.

From €399/night

View deal →Ad

Staypineapple, An Iconic Hotel, The Loop

★ 8.8(162)· 4★ hotel· Free wifi

From €400/night

View deal →Ad

The Godfrey Hotel Chicago

★ 8.7(384)· 4.5★ hotel· Free wifi

From €421/night

View deal →Ad

The Royal Sonesta Chicago River North

★ 8.6(150)· 4.5★ hotel· Breakfast incl.

From €425/night

View deal →Ad

Trump International Hotel & Tower Chicago

★ 9.0(250)· 5★ hotel· Free wifi

From €458/night

View deal →Ad

Viceroy Chicago

★ 9.2(28)· 4.5★ hotel· Free wifi

From €465/night

View deal →Ad

Sofitel Chicago Magnificent Mile

★ 9.1(441)· 4.5★ hotel· Free wifi· Breakfast incl.

From €474/night

View deal →Ad

The Westin Chicago River North

★ 8.7(17)· 4.5★ hotel

From €485/night

View deal →Ad

Park Hyatt Chicago

★ 8.3(8)· 5★ hotel· Breakfast incl.

From €638/night

View deal →Ad

The Ritz-Carlton, Chicago

Waldorf Astoria Chicago

★ 8.4(24)· 5★ hotel· Free wifi· Breakfast incl.

From €712/night

View deal →Ad

Real listings from our booking partner, priciest first — sample rates for 2026-08-22 to 2026-08-23. Use the search box above for your own dates.

Map of luxury hotels in Chicago

Map data © OpenStreetMap contributors.

Weather in Chicago by season

Based on the last 3 years of real historical data.

January

0° / -7°C

~77mm rain

April

16° / 5°C

~87mm rain

July

29° / 19°C

~176mm rain

October

18° / 10°C

~75mm rain

Things to do near Chicago hotels

Chicago Architecture Center River Cruise aboard First Lady

★ 4.9(6,498 reviews)· 1h 30m

From €51

Chicago Architecture River Cruise

★ 4.8(16,599 reviews)· 1h 30m

From €35

Chicago River 90-Minute Architecture Tour

★ 4.7(10,512 reviews)· 1h 30m

From €40

Chicago River 45-Minute Architecture Tour from Magnificent Mile

★ 4.7(3,406 reviews)· 45 min

From €25

Real listings from Viator, including live ratings and prices — clicking through takes you to book directly.

More hotel options in Chicago

See all hotels in Chicago 5-Star Hotels in Chicago Cheap Hotels in Chicago Flights to Chicago Chicago travel guide Things to do in Chicago Weekend in Chicago Pick your own dates →

Continue planning your trip to Chicago

Same destination, real availability — no need to search again.

Search hotels in Chicago Find activities in Chicago Rent a car

FAQs — Luxury Hotels in Chicago

Based on 21 real live listings we checked, luxury hotels in Chicago average around €458 a night, with the cheapest we found at €356. Use the search box above for pricing on your exact dates.