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 $193 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.

Fri, Jan 15 - Mon, Jan 18
SJU
San Juan
ORD
Chicago
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 15 from San Juan to Chicago, returning Mon, Jan 18, priced at $193 found 1 day ago
Wed, Dec 2 - Mon, Dec 7
SJU
San Juan
ORD
Chicago
$196 Roundtrip, found 4 days ago
$196
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Dec 2 from San Juan to Chicago, returning Mon, Dec 7, priced at $196 found 4 days ago
Fri, Jan 15 - Mon, Jan 18
SJU
San Juan
ORD
Chicago
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Jan 15 from San Juan to Chicago, returning Mon, Jan 18, priced at $197 found 1 day ago
Fri, Dec 4 - Sun, Dec 6
SJU
San Juan
MDW
Chicago
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from San Juan to Chicago, returning Sun, Dec 6, priced at $212 found 4 days ago
Fri, Jan 15 - Mon, Jan 18
SJU
San Juan
ORD
Chicago
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jan 15 from San Juan to Chicago, returning Mon, Jan 18, priced at $212 found 1 day ago
Thu, Nov 19 - Mon, Nov 30
SJU
San Juan
ORD
Chicago
$216 Roundtrip, found 6 days ago
$216
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Nov 19 from San Juan to Chicago, returning Mon, Nov 30, priced at $216 found 6 days 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
$129 nightly
The price is $153 total per night from Nov 10 to Nov 11
$153 total
Nov 10 - Nov 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
$122 nightly
The price is $145 total per night from Nov 22 to Nov 23
$145 total
Nov 22 - Nov 23
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$116 nightly
The price is $138 total per night from Nov 23 to Nov 24
$138 total
Nov 23 - Nov 24
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.
Opens in a new windowRiver Hotel
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The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
$119 nightly
The price is $141 total per night from Nov 23 to Nov 24
$141 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
8.6/10 Excellent! (2,175 reviews)
"Have fun"

Reviewed on Oct 26, 2026

Opens in a new windowThe Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$134 nightly
The price is $159 total per night from Nov 2 to Nov 3
$159 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8/10 Very Good! (2,480 reviews)
"Hotel was"

Reviewed on Oct 27, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$133 nightly
The price is $158 total per night from Nov 27 to Nov 28
$158 total
Nov 27 - Nov 28
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.
Opens in a new windowHilton Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
$119 nightly
The price is $141 total per night from Nov 22 to Nov 23
$141 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Opens in a new windowTHE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$212 nightly
The price is $248 total per night from Nov 22 to Nov 23
$248 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Opens in a new windowHilton Chicago O'Hare Airport
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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.

Top Picks

*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.