Romantic Vacations in Far Southeast Side 2026

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Flight and Romantic hotel deals in Far Southeast Side

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

Fairmont Chicago at Millennium Park

Downtown Chicago

CA $790

per person

Sep 26 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (2,293 reviews)

Four Seasons Hotel Chicago

Downtown Chicago

CA $6,031

per person

Oct 7 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,393

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,152

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on Aug 19, 2026

L7 Chicago by LOTTE

Downtown Chicago

CA $2,762

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (4,495 reviews)

Coffee in lobby was good amenity . Valet were super nice and helpful. Breakfast was amazing

Reviewed on Aug 20, 2026

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5* Romantic holidays in Far Southeast Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,674

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,960 reviews)

A+

Reviewed on Aug 20, 2026

Four Seasons Hotel Chicago

Downtown Chicago

CA $6,031

per person

Oct 7 - Oct 13

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Reviewed on Aug 16, 2026

The Peninsula Chicago

Downtown Chicago

CA $2,106

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

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3 Night Romantic holidays in Far Southeast Side

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

Level Chicago – Old Town

Downtown Chicago

CA $1,152

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on Aug 19, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,275

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Swissotel - Chicago

Downtown Chicago

CA $1,207

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

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4 Night Romantic holidays in Far Southeast Side

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

Swissotel - Chicago

Downtown Chicago

CA $1,279

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,675

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Level Chicago Fulton Market

Downtown Chicago

CA $1,393

per person

Oct 27 - Oct 31

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Reviewed on Aug 17, 2026

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

When booking a romantic Far Southeast 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 Far Southeast 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 Far Southeast 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 $790 and can enjoy savings of up to 29 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 Far Southeast 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 Far Southeast 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 Far Southeast Side.

Can I book a romantic Far Southeast 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 Far Southeast Side search.

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

Several romantic Far Southeast 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.