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
May 2026
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
$327
31
Low
$228
Cheapest day
Cheaper
Mid
Priciest
Hotels for Tue, Jun 23
Sort
Cheapest first
Top rated
Most reviewed
Belveder Grand
9.5
Excellent · 3,627 reviews
$249
$249/night · 1n
Book
Riverside Luxury Collection
9.8
Excellent · 2,103 reviews
$411
$411/night · 1n
Book
The Meridian Royal
9.2
Excellent · 3,722 reviews
$460
$460/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