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 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
$209
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
$180
Picture of Crowne Plaza Chicago West Loop in Chicago

Crowne Plaza Chicago West Loop

(1700 yards to city center)
  • 3.5 stars
Excellent 4.1 / 5
from$179
$143
Picture of Dana Hotel and Spa in Chicago

Dana Hotel and Spa

(1600 yards to city center)
  • 4 stars
Excellent 4.5 / 5
from
$186
Picture of InterContinental Chicago Magnificent Mile in Chicago

InterContinental Chicago Magnificent Mile

(1300 yards to city center)
  • 4.5 stars
Excellent 4.2 / 5
from
$187
Picture of The Drake, a Hilton Hotel in Chicago

The Drake, a Hilton Hotel

(1.4 miles to city center)
  • 4 stars
Excellent 4.4 / 5
from
$209
Picture of Thompson Chicago in Chicago

Thompson Chicago

(1.4 miles to city center)
  • 4.5 stars
Outstanding 4.7 / 5
from$229
$183
Picture of Hotel Chicago Downtown, Autograph Collection in Chicago

Hotel Chicago Downtown, Autograph Collection

(930 yards to city center)
  • 4 stars
Excellent 4.4 / 5
from
$179
Picture of Kimpton Hotel Monaco Chicago in Chicago

Kimpton Hotel Monaco Chicago

(750 yards to city center)
  • 4.5 stars
Outstanding 4.6 / 5
from$189
$151
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
$199
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
$199
Picture of W Chicago - City Center in Chicago

W Chicago - City Center

(500 yards to city center)
  • 4 stars
Good 3.8 / 5
from
$220
Picture of Kimpton Hotel Palomar Chicago in Chicago

Kimpton Hotel Palomar Chicago

(1200 yards to city center)
  • 4.5 stars
Outstanding 4.6 / 5
from$229
$206
Picture of Trump International Hotel & Tower Chicago in Chicago

Trump International Hotel & Tower Chicago

(1000 yards to city center)
  • 5 stars
Outstanding 4.7 / 5
from$375
$316
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
$83
Picture of JW Marriott Chicago in Chicago

JW Marriott Chicago

(480 yards to city center)
  • 4 stars
Outstanding 4.6 / 5
from
$259
Picture of Staypineapple at The Alise Chicago in Chicago

Staypineapple at The Alise Chicago

(290 yards to city center)
  • 4 stars
Outstanding 4.6 / 5
from$179
$161
Picture of The Ritz-Carlton, Chicago in Chicago

The Ritz-Carlton, Chicago

(1.2 miles to city center)
  • 5 stars
Outstanding 4.6 / 5
from
$289
Picture of The Peninsula Chicago in Chicago

The Peninsula Chicago

(1.0 mile to city center)
  • 5 stars
Outstanding 4.9 / 5
from
$399
Picture of Carleton of Oak Park in Oak Park

Carleton of Oak Park

(9.0 miles to city center)
  • 3 stars
Excellent 4.1 / 5
from
$134
Picture of Waldorf Astoria Chicago in Chicago

Waldorf Astoria Chicago

(1.3 miles to city center)
  • 5 stars
Outstanding 4.7 / 5
from
$392
Picture of The Blackstone, Autograph Collection in Chicago

The Blackstone, Autograph Collection

(970 yards to city center)
  • 4 stars
Excellent 4.5 / 5
from
$239
Picture of Four Seasons Hotel Chicago in Chicago

Four Seasons Hotel Chicago

(1.3 miles to city center)
  • 5 stars
Outstanding 4.7 / 5
from
$400
Picture of Park Hyatt - Chicago in Chicago

Park Hyatt - Chicago

(1.1 miles to city center)
  • 5 stars
Outstanding 4.7 / 5
from
$326
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
$275

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