Best Flight From Luis Munoz Marin Intl. To CHI

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Amazing SJU to CHI Flight Deals

The cheapest flights to CHI-All Airports were $192 for round trip flights and $79 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 22 - Sun, Oct 25
SJU
San Juan
MDW
Chicago
$192 Roundtrip, found 11 hours ago
$192
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Oct 22 from San Juan to Chicago, returning Sun, Oct 25, priced at $192 found 11 hours ago
Fri, Dec 18 - Sat, Jan 9
SJU
San Juan
ORD
Chicago
$204 Roundtrip, found 7 hours ago
$204
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Dec 18 from San Juan to Chicago, returning Sat, Jan 9, priced at $204 found 7 hours ago
Wed, Oct 14 - Sat, Oct 17
SJU
San Juan
ORD
Chicago
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Oct 14 from San Juan to Chicago, returning Sat, Oct 17, priced at $217 found 11 hours ago
Thu, Oct 22 - Tue, Oct 27
SJU
San Juan
ORD
Chicago
$222 Roundtrip, found 2 hours ago
$222
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Oct 22 from San Juan to Chicago, returning Tue, Oct 27, priced at $222 found 2 hours ago
Thu, Oct 22 - Tue, Oct 27
SJU
San Juan
ORD
Chicago
$226 Roundtrip, found 2 hours ago
$226
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Oct 22 from San Juan to Chicago, returning Tue, Oct 27, priced at $226 found 2 hours ago
Thu, Oct 1 - Tue, Oct 6
SJU
San Juan
ORD
Chicago
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 1 from San Juan to Chicago, returning Tue, Oct 6, priced at $228 found 1 day ago

Hotels near CHI-All Airports Airport (CHI)

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$170 nightly
The price is $202 total per night from Sep 10 to Sep 11
$202 total
Sep 10 - Sep 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$152 nightly
The price is $181 total per night from Sep 29 to Sep 30
$181 total
Sep 29 - Sep 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
9.4/10 Exceptional! (890 reviews)
"Great spot!"

Reviewed on Sep 7, 2026

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Opens in a new windowKasa Magnificent Mile Chicago
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River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$181 nightly
The price is $216 total per night from Sep 27 to Sep 28
$216 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
8.8/10 Excellent! (5,409 reviews)
"I didn’t drive in so this was a great location. Staff was friendly. Small room as expected. Met all needs. Main highlight is the location"

Reviewed on Sep 9, 2026

Opens in a new windowRiver Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
$203 nightly
The price is $242 total per night from Sep 20 to Sep 21
$242 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8/10 Very Good! (1,588 reviews)
"Our AC thermostat didnt go below 76. With a heat index of over 100, was not a comfortable stay. Alerted front desk after first night, they said an engineer would look at it but we never heard anything. All we know is 2nd night was no better."

Reviewed on Sep 9, 2026

Opens in a new windowHampton Inn Chicago Downtown/Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$224 nightly
The price is $266 total per night from Sep 10 to Sep 11
$266 total
Sep 10 - Sep 11
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
8.6/10 Excellent! (3,168 reviews)
"The floor we stayed on was outdated and a bit run down and dingy. Staff were too concerned with VIPs to be helpful and accommodating to my disabled husband. The room wouldn't get cooler than 70 degrees and the ice machine was down our entire 5 day stay. Everything was overpriced and confusing."

Reviewed on Sep 9, 2026

Opens in a new windowHilton Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
$312 nightly
The price is $371 total per night from Sep 10 to Sep 11
$371 total
Sep 10 - Sep 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
9.4/10 Exceptional! (3,536 reviews)
"amazing hotel"

Reviewed on Sep 9, 2026

Opens in a new windowHyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
$311 nightly
The price is $370 total per night from Sep 27 to Sep 28
$370 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
9.6/10 Exceptional! (4,766 reviews)
"Our 3rd stay at Lotte. Great area to be close to the Riverwalk, restaurants and shopping!"

Reviewed on Sep 9, 2026

Opens in a new windowL7 Chicago by LOTTE
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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.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.