Best Flight From Bradley Intl. To CHI

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Amazing BDL to CHI Flight Deals

The cheapest flights to CHI-All Airports were $222 for round trip flights and $111 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Nov 18 - Wed, Nov 25
BDL
Hartford
ORD
Chicago
$222 Roundtrip, found 4 hours ago
$222
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Wed, Nov 18 from Hartford to Chicago, returning Wed, Nov 25, priced at $222 found 4 hours ago
Sun, Jan 31 - Sat, Feb 6
BDL
Hartford
ORD
Chicago
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sun, Jan 31 from Hartford to Chicago, returning Sat, Feb 6, priced at $227 found 3 days ago
Wed, Nov 11 - Wed, Nov 18
BDL
Hartford
ORD
Chicago
$232 Roundtrip, found 4 hours ago
$232
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Wed, Nov 11 from Hartford to Chicago, returning Wed, Nov 18, priced at $232 found 4 hours ago
Sun, Jan 31 - Fri, Feb 5
BDL
Hartford
ORD
Chicago
$233 Roundtrip, found 3 days ago
$233
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sun, Jan 31 from Hartford to Chicago, returning Fri, Feb 5, priced at $233 found 3 days ago
Wed, Nov 18 - Sun, Nov 22
BDL
Hartford
ORD
Chicago
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Nov 18 from Hartford to Chicago, returning Sun, Nov 22, priced at $247 found 1 day ago
Sat, Nov 21 - Sun, Nov 22
BDL
Hartford
ORD
Chicago
$252 Roundtrip, found 6 days ago
$252
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Sat, Nov 21 from Hartford to Chicago, returning Sun, Nov 22, priced at $252 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.