Far Southwest Side Romantic Holidays

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Top flight + Romantic hotel deals in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£802
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,364
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£975
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,039
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (2,169 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£872
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
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5* Romantic holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,364
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£1,625
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£2,525
per person
26 Oct - 31 Oct
found 15 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The hotel is located in a prime location with shops and restaurants nearby. The staff was very accommodating and helpful.

Reviewed on 15 Sept 2026

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3 Night Romantic holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
£982
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Awesome

Reviewed on 15 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£989
per person
1 Dec - 4 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,117
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Lovely room

Reviewed on 15 Sept 2026

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4 Night Romantic holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£860
per person
26 Nov - 30 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,005
per person
26 Nov - 30 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,120
per person
1 Nov - 5 Nov
found 1 hour ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I was excited to stay here and I truly never leave negative reviews, but others should avoid making the same mistake I did paying for this hotel. The staff was very nice and the property looks nice, but it's extremely overpriced. Don't be fooled into paying more for the amenities because none of them work!! - There was no deadbolt on the hotel room door. If I'm paying $200+ a night, I shouldn't have to barricade the door every night. The balcony door was also unlocked when I arrived. - No hangers or lotion in the room. - Sauna and hot tub were "closed for cleaning" for three full days of my stay. - I needed to consent to a background check in order to confirm my reservation. I called to confirm this because I found it incredibly invasive and unnecessary. Turns out it was real. Wild. Also, there is a $200 PER NIGHT deposit upon arrival. I travel often and I've never seen that before. - Nonexistent water pressure in the shower. And someone's trash was left in the shower when I arrived. - Washing machine reeked of mold and was therefore unusable. - TV and oven didn't work Overall, if this hotel was $60-80 a night, it'd be great. But, it's a total waste of money. Again, the staff was very nice and helpful (I didn't even include the things they resolved for me during my stay) but I'm not going to bother them about every single amenity that is supposedly included with the room. The things that would make this hotel worth the money are unfortunately all a facade.

Reviewed on 15 Sept 2026

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How to find a romantic Far Southwest Side holiday

How can I find the best Far Southwest Side vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Far Southwest Side. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Far Southwest Side romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Far Southwest Side that start from £802. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Far Southwest Side romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Far Southwest Side?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Far Southwest Side?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Far Southwest Side that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Far Southwest Side with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Far Southwest Side romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Far Southwest Side

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.