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Top Honeymoon vacation packages in Chicago

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

₩658,370

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

8.2/10 Very Good! (2,365 reviews)

There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Downtown Chicago

Save 100% on your flight

₩868,557

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

9.6/10 Exceptional! (1,067 reviews)

always clean, great staff comfortable beds good location

Reviewed on Feb 1, 2026

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

₩921,901

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

8.6/10 Excellent! (2,008 reviews)

Staff was amazing throughout our stay. Room very clean, property well maintained. Great location

Reviewed on Feb 1, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

₩1,527,398

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

₩942,281

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

9.4/10 Exceptional! (3,392 reviews)

Friendly staff, accommodating- we arrived earlier than our check-in time and they were able to get us in our room promptly.

Reviewed on Feb 3, 2026

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5* Honeymoon vacations in Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

₩1,527,398

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

₩2,222,480

per person

Apr 24 - Apr 29

found 1 day ago

Roundtrip flight included

New York (JFK) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

The amenities and staff are top tier!!!

Reviewed on Feb 1, 2026

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Top Honeymoon Chicago Hotels

Eurostars Magnificent Mile

660 North State Street Chicago IL

9 min drive from Wrigley Field

Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...

8.8/10 Excellent! (3,208 reviews)

Great rooms and easy check in. Can’t believe I haven’t stayed here before. I’ll be be back!

Reviewed on Feb 4, 2026

The Wade

644 N Lake Shore Dr Chicago IL

10 min drive from Wrigley Field

Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...

8.4/10 Very Good! (1,647 reviews)

Room was nice a little dated but I still enjoyed the room it was really clean room service was nice. Pool was nice and empty

Reviewed on Jan 31, 2026

Hyatt Lodge Oak Brook Chicago

2815 Jorie Blvd Oak Brook IL

30 min drive from Wrigley Field

Book a stay at this spa hotel in Oak Brook. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...

8.8/10 Excellent! (1,006 reviews)

Staff were all warm and welcoming. The pool/spa area was gorgeous and clean.

Reviewed on Feb 3, 2026

See all 5,769 properties in Chicago

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.