Hotel
Dip
Luxury
Cheap
Guides
Sign in
Sign up free
Home
/ Chicago
Cheapest dates for romantic hotels in Chicago
Stay flexible and book the dip. Greener days are cheaper, so tap a day to see hotels.
Destination
Hotel class
5-star (luxury)
4-star+
3-star+
Any class
When
May 29 to Aug 29 · Any length
Update
More filters
1
Vibe and amenities
Boutique
Beachfront
Waterfront
Pet-friendly
Adults-only
Spa
Romantic
Pool
Family-friendly
Minimum guest rating
Any rating
8.0+ Very good
9.0+ Excellent
Cheapest stays in the next 3 months
1 night
from Mon, Jun 8 · $138/night
$138
June 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
$261
2
$253
3
$245
4
$179
5
$359
6
$352
7
$246
8
Low
$138
9
$280
10
$232
11
$268
12
$249
13
$364
14
$234
15
$242
16
$168
17
$281
18
$267
19
$333
20
$318
21
$283
22
$257
23
$249
24
$162
25
$307
26
$336
27
$329
28
$248
29
30
Cheapest day
Cheaper
Mid
Priciest
Hotels for Mon, Jun 8
Sort
Cheapest first
Top rated
Most reviewed
Belveder Grand
9.5
Excellent · 3,627 reviews
$138
$138/night · 1n
Book
Riverside Luxury Collection
9.8
Excellent · 2,103 reviews
$418
$418/night · 1n
Book
The Meridian Royal
9.2
Excellent · 3,722 reviews
$455
$455/night · 1n
Book
More for Chicago
All Chicago hotels
Best time to visit Chicago
Luxury in Chicago
5-star in Chicago
Cheap in Chicago
Beachfront in Chicago
Spa in Chicago
Pet-friendly in Chicago