Romantic Hotels in South Loop, IL

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Top South Loop Romantic Getaways & Hotels

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4 out of 5
500 South Dearborn Street Chicago IL
Free Cancellation
$95 nightly
The price is $112 total per night
$112 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
If a romantic getaway is the plan, you're sure to love the premium mattresses and Egyptian cotton sheets at this boutique hotel. You'll also appreciate the restaurant, ...
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
636 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $179 total per night
$179 total
Dec 21 - Dec 22
Total with taxes and fees
Fall in love again at this Beaux Arts hotel. You and your special someone are sure to love the spa services, in-room massages, and lobby fireplace. You'll also ...
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$199 nightly
The price is $234 total per night
$234 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this romantic hotel, featuring in-room massages and al fresco dining. Couples will appreciate the premium mattresses, luxury bedding, and 2 ...
The Wheeler Mansion

The Wheeler Mansion

4 out of 5
2020 South Calumet Avenue Chicago IL
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Ready for a romantic getaway? You are sure to enjoy the garden, lobby fireplace, and premium mattresses at this boutique hotel. You'll also appreciate the luxury ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $163 total per night
$163 total
Dec 21 - Dec 22
Total with taxes and fees
Fall in love again at this historic hotel. You and your special someone are sure to love the hot tub, 2 restaurants, and lobby fireplace. You'll also appreciate ...
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $136 total per night
$136 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Plan a stay with your special someone, where you're sure to love the soaking tubs and 2 restaurants at this romantic hotel. You'll also appreciate the 2 ...
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $99 total per night
$99 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Onsite dining and more await visiting couples at this romantic hotel.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

South Loop hotels essential information

Accommodation
4,760 hotels
Lowest Price
$99
Highest Price
$234
Popular hotels
The Blackstone, Autograph Collection, Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel, Hyatt Regency McCormick Place Chicago , Congress Plaza Hotel, Hilton Chicago, The Wheeler Mansion, Travelodge by Wyndham Downtown Chicago

Recent South Loop hotel reviews by fellow wanderers

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"great stay"
A verified traveler stayed at Palmer House a Hilton Hotel
Palmer House a Hilton Hotel

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