West Side Romantic Vacations

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Flight and Romantic hotel deals in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $861
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,557
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,469
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Clean room

Reviewed on Aug 15, 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
CA $1,491
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Highlights Loved everything about this space! Just look at this breathtaking view. Photos and videos can’t even come close to the real thing. Washer and dryer, fully functional kitchen with nespresso maker, beautiful bathrooms, super comfortable beds, impressively quiet, and the balcony! Perfect location for walking (or short uber ride) to everything. Rooftop pool and hot tub were amazing. Rooms The rooms were massive, beds were so comfortable, and had everything we needed. Location It’s in a perfect location for walking and enjoying the city, without being over crowded. Parking The parking was the only struggled; you have to call and hope someone at the front desk will answer to let you into the garage. It took several calls and walking back into the lobby to get access. Can improve We also didn’t get our free bottle of wine that was promoted on the Expedia listing. There were a lot of spiders on the balcony, but they were harmless web spinners. Amenities The rooftop pool and hot tub added an extra layer of fun to the experience. We didn’t get a chance to experience the arcade, but that was a cool amenity. Noise level Super quiet. The staff Super impressed with the staff, who read my note about this being a special trip, and then giving us a room that exceeding our expectations.

Reviewed on Aug 14, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,167
per person
Oct 20 - Oct 23
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Aug 14, 2026

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5* Romantic holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
CA $2,408
per person
Oct 19 - Oct 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $3,362
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,160
per person
Oct 19 - Oct 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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3 Night Romantic holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $1,043
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,266
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $1,989
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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4 Night Romantic holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $1,152
per person
Oct 19 - Oct 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,655
per person
Oct 19 - Oct 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,421
per person
Oct 19 - Oct 23
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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 Aug 12, 2026

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Plan unforgettable romantic West Side vacations

What are some of the benefits of booking a romantic West Side vacation?

When booking a romantic West Side vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Chicago.

How can I find the best vacation packages for couples?

If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the West Side destination, and you'll be met with an array of options for you and your partner to enjoy.

Can I find cheap romantic vacations for 2 in West Side?

Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $861 and can enjoy savings of up to 28 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first.

What do I need to consider when booking a romantic getaway in West Side?

Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout West Side certainly come in handy here.

What amenities should I look for in a luxury romantic vacation?

If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to West Side.

Can I book a romantic West Side vacation with a hot tub?

Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them.

How can I find romantic vacation getaways that are all-inclusive?

An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your West Side search.

Can I book a romantic trip to West Side that is fully refundable?

Several romantic West Side vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements.

Why should I book a romantic vacation with Expedia?

Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in West Side

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.