For couples · Chicago · United States
Romantic things to do in Chicago
Ideas for a couples' trip, from small moments to a special day out.
Updated By the AMZBooking editorial team
Photo: ajay_suresh, CC BY 2.0
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Quick answer
Chicago's romance is in its skyline: sunset from the water or a high-rise, jazz in a dim lounge, and long walks by the lake. Early autumn evenings are the sweet spot, warm enough for the river and quiet enough for a table. Couples tend to stay in Gold Coast and Old Town.
Key facts
- Romantic ideas
- 6
- Couple-friendly sights
- 4
- Area for couples
- Gold Coast and Old Town
- Best months
- May–June and September–October
Romantic ideas
1.Sunset architecture cruise
An evening river cruise shows the towers glowing at dusk and lit up after dark.
2.Jazz at the Green Mill
The Uptown lounge, with a history going back to the Prohibition era, has live jazz most nights in a dark, velvet-boothed room.
3.Drinks with a view at 360 Chicago
Watch the lights come on along Lake Shore Drive from the 94th floor of 875 North Michigan Avenue.
4.Promontory Point at dusk
This lakefront peninsula in Hyde Park has one of the best views back to the skyline, with stone council rings for sitting.
5.Lily Pool in Lincoln Park
The Alfred Caldwell Lily Pool is a quiet Prairie-style garden near the zoo, designed for slow walks.
6.Dinner on Randolph Street
Book a table in the West Loop and finish with a cocktail at a rooftop bar overlooking the Loop.
Sights couples love
Experience · Chicago River
Chicago Architecture Center river cruise
Sit on the open upper deck and bring a layer even in summer; it is several degrees cooler on the water.
- Time needed
- About 75–90 minutes
- Cost
- Mid-priced
- Iconic
- Architecture
- Views
- Couples
- Photo spot
Experience · Old Town
The Second City
Stay after the late show for the improv set, where the cast tests new material from audience suggestions.
- Time needed
- 2 hours
- Cost
- Mid-priced
- After dark
- Couples
- Iconic
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Viewpoint · Streeterville
360 Chicago observation deck
Pick this over the Skydeck if you want lake and beach views; the Skydeck looks more over the city grid and the west.
- Time needed
- 1 hour
- Cost
- Mid-priced
- Views
- Couples
- After dark
Waterfront · The Loop
Chicago Riverwalk
Look into the McCormick Bridgehouse & Chicago River Museum in the DuSable Bridge tower to see the gears that raise the bridge; it opens seasonally.
- Time needed
- 1–2 hours
- Cost
- Free
- Free
- Couples
- After dark
- Food
- Outdoors
Where couples should stay
$$$$ · Best for couples, luxury and quiet stays
Gold Coast and Old Town
The Gold Coast holds some of Chicago's grandest late-19th-century homes along Astor Street, the luxury boutiques of Oak Street and the bars of Rush and Division streets. Old Town, just to the west, has Victorian cottages, the Second City comedy theatre on Wells Street and the Old Town Ale House. Oak Street Beach and the southern end of Lincoln Park are both a short walk away.
- Good
- Elegant, leafy residential streets; Close to Oak Street Beach and Lincoln Park; Comedy clubs and classic taverns nearby
- Watch out
- High hotel prices; Rush Street bars get rowdy late at weekends
- Nearby
- Oak Street Beach, The Second City, Lincoln Park, Astor Street
Romantic day trips
- Chicago Botanic Garden (About 1 hour by train and a short walk) — Spread across islands in the northern suburb of Glencoe, the garden includes the Malott Japanese Garden, a rose garden, a fruit and vegetable garden and walking paths around the lagoons.
- Galena (About 3 hours by car) — A preserved 19th-century river town in the hills of northwest Illinois, with a brick Main Street of shops and restaurants and the home of Ulysses S.
For dinner
Share local specialities such as Deep-dish pizza, Tavern-style thin-crust pizza and Italian beef. Many casual places such as hot-dog and beef stands are counter-service; you order, pay and collect at the counter.
Questions travellers ask
+Is Chicago romantic?
Chicago's romance is in its skyline: sunset from the water or a high-rise, jazz in a dim lounge, and long walks by the lake. Early autumn evenings are the sweet spot, warm enough for the river and quiet enough for a table.
+What is the most romantic thing to do in Chicago?
Sunset architecture cruise: An evening river cruise shows the towers glowing at dusk and lit up after dark.
+Where should couples stay in Chicago?
Gold Coast and Old Town: Mansions on Astor Street, Oak Street boutiques and comedy on Wells Street.