Romantic Hotels in Chicago

  • Pay now or later on most rooms
  • Free cancellation on most rooms
  • Price Guarantee

Collect 10 nights get 1 free*

And look out for Secret Prices on select hotels

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FREE
Picture of Hotel Blake, an Ascend Hotel Collection Member in Chicago

Hotel Blake, an Ascend Hotel Collection Member

(710 yards to city center)
  • 3.5 stars
Excellent 4.5 / 5
from
$209
Picture of Hotel Chicago Downtown, Autograph Collection in Chicago

Hotel Chicago Downtown, Autograph Collection

(930 yards to city center)
  • 4 stars
Excellent 4.5 / 5
from
$229
Picture of Fairmont Chicago at Millennium Park in Chicago

Fairmont Chicago at Millennium Park

(920 yards to city center)
  • 4.5 stars
Excellent 4.3 / 5
from
$369
Picture of Carleton of Oak Park in Oak Park

Carleton of Oak Park

(9 miles to city center)
  • 3 stars
Excellent 4.2 / 5
from
$134
Picture of Thompson Chicago in Chicago

Thompson Chicago

(1.4 miles to city center)
  • 4.5 stars
Outstanding 4.8 / 5
from$329
$319
Picture of The Ritz-Carlton, Chicago in Chicago

The Ritz-Carlton, Chicago

(1.2 miles to city center)
  • 5 stars
Excellent 4.5 / 5
from
$299
Picture of Raffaello Hotel in Chicago

Raffaello Hotel

(1.3 miles to city center)
  • 4 stars
Excellent 4.2 / 5
from
$229
Picture of Waldorf Astoria Chicago in Chicago

Waldorf Astoria Chicago

(1.3 miles to city center)
  • 5 stars
Outstanding 4.6 / 5
from
$301
Picture of Park Hyatt - Chicago in Chicago

Park Hyatt - Chicago

(1.1 miles to city center)
  • 5 stars
Outstanding 4.7 / 5
from
$345
Picture of Sofitel Chicago Magnificent Mile in Chicago

Sofitel Chicago Magnificent Mile

(1.2 miles to city center)
  • 4.5 stars
Outstanding 4.6 / 5
from
$251
Picture of The Champagne Lodge & Luxury Suites in Willowbrook

The Champagne Lodge & Luxury Suites

(19 miles to city center)
  • 3.5 stars
Excellent 4.2 / 5
from
$106
Picture of W Chicago - City Center in Chicago

W Chicago - City Center

(500 yards to city center)
  • 4 stars
Good 3.8 / 5
from
$264
Picture of JW Marriott Chicago in Chicago

JW Marriott Chicago

(480 yards to city center)
  • 4 stars
Outstanding 4.6 / 5
from
$239
Picture of Radisson Blu Aqua Hotel Chicago in Chicago

Radisson Blu Aqua Hotel Chicago

(980 yards to city center)
  • 4.5 stars
Excellent 4.5 / 5
from
$220
Picture of Swissotel - Chicago in Chicago

Swissotel - Chicago

(1100 yards to city center)
  • 4.5 stars
Excellent 4.4 / 5
from$209
$157
Picture of Dana Hotel and Spa in Chicago

Dana Hotel and Spa

(1600 yards to city center)
  • 4 stars
Excellent 4.5 / 5
from
$195
Picture of Hyatt Centric Chicago Magnificent Mile in Chicago

Hyatt Centric Chicago Magnificent Mile

(1700 yards to city center)
  • 4 stars
Outstanding 4.6 / 5
from
$198
Picture of The Blackstone, Autograph Collection in Chicago

The Blackstone, Autograph Collection

(970 yards to city center)
  • 4 stars
Excellent 4.5 / 5
from
$329
Picture of InterContinental Chicago Magnificent Mile in Chicago

InterContinental Chicago Magnificent Mile

(1300 yards to city center)
  • 4.5 stars
Excellent 4.3 / 5
from
$280
Picture of The Westin Michigan Avenue Chicago in Chicago

The Westin Michigan Avenue Chicago

(1.3 miles to city center)
  • 4.5 stars
Excellent 4.4 / 5
from
$272
Picture of The Drake, a Hilton Hotel in Chicago

The Drake, a Hilton Hotel

(1.4 miles to city center)
  • 4 stars
Excellent 4.3 / 5
from
$277
Picture of theWit Chicago - a DoubleTree by Hilton Hotel in Chicago

theWit Chicago - a DoubleTree by Hilton Hotel

(630 yards to city center)
  • 4.5 stars
Excellent 4.4 / 5
from
$249
Picture of The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago in Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

(1300 yards to city center)
  • 4.5 stars
Excellent 4.5 / 5
from
$419
Picture of Harvey House Bed & Breakfast in Oak Park

Harvey House Bed & Breakfast

(8.3 miles to city center)
  • 4 stars
Outstanding 4.9 / 5
from
$205
Picture of Hampton Inn Chicago Downtown/Magnificent Mile in Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

(1 mile to city center)
  • 2.5 stars
Excellent 4.3 / 5
from
$192

Collect 10 nights get 1 free*

And look out for Secret Prices on select hotels

  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
=
FREE