Central Chicago Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

Photo by Phil Ostroff
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Top flight + Romantic hotel deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,351
per person
17 Oct - 24 Oct
found 3 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on 12 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,353
per person
28 Sept - 4 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Rooms were clean and staff very helpful. Really enjoyed the roof top restaurant

Reviewed on 15 Aug 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
£1,402
per person
17 Oct - 24 Oct
found 3 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Hotel amenities were great, and the suite was nice enough. The mattress was a little springy, but not terrible. I was frustrated by finding out about an amenities fee at the end that added roughly $100 to my cost at the hotel. That felt a lot like the “hidden fee” that so many booking services seek to advertise not having. That hotel would probably say that they don’t hide that fee, that it’s stated in the hotel stay conditions or something to that affect; but I’d argue that most people staying there for the first time are probably unaware of the fee prior to coming. If they want to charge an additional amount for the amenities at the hotel (which I admit are great), put the cost for the amenities into the price per night for the room itself. If you advertise the amenities at the hotel as a perk of staying there, consider that part of the upfront price rather than something that’s informed to you as you check out.

Reviewed on 14 Aug 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
Save 100% on your flight
£1,628
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,167
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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5* Romantic holidays in Central Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,379
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,167
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
Save 100% on your flight
£2,528
per person
17 Oct - 24 Oct
found 3 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Dublin to Central Chicago
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3 Night Romantic holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

Downtown Evanston
£1,028
per person
21 Sept - 24 Sept
found 8 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (99 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£1,792
per person
21 Sept - 24 Sept
found 8 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare
£1,066
per person
21 Sept - 24 Sept
found 8 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very good! (2,362 reviews)
Bathroom smelled horrible for the first few hours I was there.

Reviewed on 15 Aug 2026

Don't see what you're looking for?
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4 Night Romantic holidays in Central Chicago

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

Hotel Riu Plaza Chicago

Downtown Chicago
£1,018
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Rooms were clean and staff very helpful. Really enjoyed the roof top restaurant

Reviewed on 15 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,096
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,379
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Don't see what you're looking for?
See all available trips from Dublin to Central Chicago
View all trips

How to find a romantic Central Chicago holiday

How can I find the best Central Chicago vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Central Chicago. 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 Central Chicago 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 Central Chicago that start from £1,018. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Central Chicago 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 Central Chicago?

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 Central Chicago?

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 Central Chicago 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 Central Chicago 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 Central Chicago 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 Central Chicago

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* 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.